Tetrazoyloxime derivative and plant disease control agent

ABSTRACT

According to the present invention, a tetrazoyloxime derivative and a salt thereof, which are excellent in a control effect against plant disease injury, and a plant disease controlling agent containing the same as an active ingredient are provided.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a Divisional of U.S. application Ser. No.12/733,023, which is the U.S. National Stage application ofPCT/JP2008/064253, filed Aug. 7, 2008, which claims priority fromJapanese application no. JP 2007-206297, filed Aug. 8, 2007.

TECHNICAL FIELD

The present invention relates to a novel tetrazoyloxime derivative, anda plant disease control agent containing the same as an activeingredient.

This application claims priority on Japanese Patent Application No.2007-206297 filed on Aug. 8, 2007, the disclosure of which isincorporated by reference herein.

BACKGROUND ART

In the cultivation of agricultural and horticultural crops, a largenumber of controlling agents have been used against crop injury.However, many of them are hardly satisfactory as controlling agentsbecause of insufficient control efficacy, restrictions on their use dueto appearance of pathogenic fungi having drug resistance, phytotoxicityor pollution on plants, or strong toxicity on humans, domestic animalsand fishes. Therefore, there has been required to develop plant diseasecontrolling agents applicable safely and having less of the drawbacksmentioned above.

Relating to the present invention, Patent Documents 1 to 3 disclosetetrazoyloxime derivatives having a structure similar to that of thecompounds of the present invention.

[Patent Document 1]

-   Japanese Unexamined Patent Application, First Publication No.    2004-131416    [Patent Document 2]-   Japanese Unexamined Patent Application, First Publication No.    2004-131392    [Patent Document 3]-   Japanese Unexamined Patent Application, First Publication No.    2003-137875

DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention

However, even the compounds described in these patent documents do nothave necessarily a sufficient control effect.

Under these circumstances of prior arts, the present invention has beenmade and an object thereof is to provide a tetrazoyloxime derivative ora salt thereof, which is excellent in a control effect against plantdisease injury, and a plant disease controlling agent containing atleast one kind of them as an active ingredient.

Means for Solving the Problems

The present inventors have synthesized a large number of tetrazoyloximederivatives and intensively studied about bioactivity thereof so as toachieve the above object, and found that the tetrazoyloxime derivativerepresented by formula (1) shown below and a salt thereof exhibit anexcellent control effect against plant disease injury, and areapplicable safely without causing phytotoxicity against useful plants.Thus, the present invention has been completed.

According to a first aspect of the present invention, tetrazoyloximederivatives of [1] to [3] shown below, or salts thereof are provided.

[1] A tetrazoyloxime derivative represented by formula (1):

wherein X represents a halogen atom, a C₁₋₈ alkyl group, a C₁₋₈ alkoxygroup, cyano group, a C₁₋₈ alkylsulfonyl group, nitro group, a C₁₋₈haloalkyl group, or an unsubstituted or substituted aryl group;n1 represents any one of integers of 0 to 5, andwhen n1 is 2 or more, X(s) may be the same or different with each other;A represents a tetrazoyl group represented by formula (2):

(in which Y represents a C₁₋₈ alkyl group), or a tetrazoyl grouprepresented by formula (3):

(in which Y is the same as defined above); andHet represents a pyridyl group represented by formula (4):

(in which R represents a halogen atom, a cyano group, a nitro group, ahydroxyl group, a thiol group, a formyl group, a carboxyl group, anunsubstituted or substituted amino group, an unsubstituted orsubstituted C₁₋₈ alkyl group, an unsubstituted or substituted C₂₋₈alkenyl group, an unsubstituted or substituted C₂₋₈ alkynyl group, anunsubstituted or substituted aryl group, an unsubstituted or substitutedheterocyclic group, OR¹, S(O)_(m)R¹, COR¹, or CO₂R¹,R¹ represents an unsubstituted or substituted amino group, anunsubstituted or substituted C₁₋₈ alkyl group, an unsubstituted orsubstituted C₃₋₈ cycloalkyl group, an unsubstituted or substituted C₂₋₈alkenyl group, an unsubstituted or substituted C₂₋₈ alkynyl group, or anunsubstituted or substituted aryl group,m represents any one of integers of 0 to 2,n2 represents any one of integers of 0 to 3, andwhen n2 is 2 or more, plural R(s) may be the same or different from eachother,when n2 is 0, Z represents a group represented by formula:Q¹C(═O)NH— (in which Q¹ represents a C₁₋₈ haloalkyl group, a C₂₋₈haloalkenyl group, a C₂₋₈ alkynyl group, a C₂₋₈ haloalkynyl group, aC₁₋₈ haloalkoxy group, a C₂₋₈ alkenyloxy group, a C₂₋₈ haloalkenyloxygroup, a C₂₋₈ alkynyloxy group, a C₂₋₈ haloalkynyloxy group, a C₁₋₈alkoxy group substituted with an alkoxycarbonylamino group, a C₁₋₈alkoxy group substituted with a C₃₋₈ cycloalkyl group, a C₁₋₈ branchedalkoxy group substituted with an unsubstituted aryl group, a C₁₋₈ alkoxygroup substituted with substituted aryl, a C₁₋₈ alkoxy group substitutedwith an unsubstituted or substituted heterocyclic group, a C₁₋₈ alkoxygroup substituted with an unsubstituted or substituted C₁₋₈ alkoxygroup, a C₁₋₈ alkoxy group substituted with an unsubstituted orsubstituted aryloxy group, an C₁₋₈ alkoxy group substituted with anunsubstituted or substituted aralkyloxy group, a C₂₋₈ alkynyloxy groupsubstituted with an unsubstituted or substituted aryl group, a C₁₋₈alkoxy group substituted with an unsubstituted or substituted C₁₋₈alkylthio group, a C₁₋₈ alkoxy group substituted with an unsubstitutedor substituted arylthio group, a C₁₋₈ alkoxy group substituted with anunsubstituted or substituted C₁₋₈ alkylsulfinyl group, a C₁₋₈ alkoxygroup substituted with an unsubstituted or substituted arylsulfinylgroup, a C₁₋₈ alkoxy group substituted with an unsubstituted orsubstituted C₁₋₈ alkylsulfonyl group, a C₁₋₈ alkoxy group substitutedwith an unsubstituted or substituted arylsulfonyl group, a C₁₋₈ alkoxygroup substituted with an amino group which is unsubstituted orsubstituted with an (unsubstituted or substituted alkyl group), a C₁₋₈alkoxy group which is substituted with an amino group substituted withan (unsubstituted or substituted aralkyl group), an unsubstituted orsubstituted aryloxy group, a C₁₋₈ alkyl group substituted with acarboxyl group, a C₁₋₈ alkyl group substituted with an amino group whichis unsubstituted or substituted with an (unsubstituted or substitutedaralkyl group), a C₁₋₈ alkyl group substituted with an amino group whichis substituted with an (unsubstituted or substituted alkyl group), aC₁₋₈ alkyl group substituted with an unsubstituted or substitutedaryloxy group, a C₁₋₈ alkyl group substituted with an acyl group, or aC₁₋₈ alkyl group substituted with an unsubstituted or substitutedheterocyclicoxy group),when n2 is 1 and R is a halogen atom, Z represents a hydrogen atom, anamino group, or a group represented by formula: Q²C(═O)NH— (in which Q²represents a hydrogen atom, a C₁₋₈ haloalkyl group, a C₂₋₈ alkenylgroup, a C₂₋₈ haloalkenyl group, a C₂₋₈ alkynyl group, a C₂₋₈haloalkynyl group, a C₁₋₈ alkoxy group, a C₁₋₈ haloalkoxy group, a C₂₋₈alkenyloxy group, a C₂₋₈ haloalkenyloxy group, a C₂₋₈ alkynyloxy group,a C₂₋₈ haloalkynyloxy group, a C₃₋₈ cycloalkyl group, a C₃₋₈cycloalkyloxy group, a C₁₋₈ alkylamino group, a C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted amino group, a C₁₋₈alkoxy group substituted with a C₃₋₈ cycloalkyl group, an unsubstitutedor substituted aralkyloxy group, a C₁₋₈ alkoxy group substituted with anunsubstituted or substituted heterocyclic group, a C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted C₁₋₈ alkoxy group, aC₁₋₈ alkoxy group substituted with an unsubstituted or substitutedaryloxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted orsubstituted aralkyloxy group, a C₂₋₈ alkynyloxy group substituted withan unsubstituted or substituted aryl group, a C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted C₁₋₈ alkylthio group, aC₁₋₈ alkoxy group substituted with an unsubstituted or substitutedarylthio group, a C₁₋₈ alkoxy group substituted with an unsubstituted orsubstituted C₁₋₈ alkylsulfinyl group, a C₁₋₈ alkoxy group substitutedwith an unsubstituted or substituted arylsulfinyl group, a C₁₋₈ alkoxygroup substituted with an unsubstituted or substituted C₁₋₈alkylsulfonyl group, C₁₋₈ alkoxy group substituted with an unsubstitutedor substituted arylsulfonyl group, an unsubstituted or substitutedaryloxy group, a C₁₋₈ alkyl group substituted with a carboxyl group, aC₁₋₈ alkyl group substituted with an unsubstituted or substituted aminogroup, a C₁₋₈ alkyl group substituted with an unsubstituted orsubstituted aryloxy group, a C₁₋₈ alkyl group substituted with anunsubstituted or substituted C₁₋₈ alkylthio group, a C₁₋₈ alkyl groupsubstituted with an unsubstituted or substituted alkoxy group, a C₁₋₈alkyl group substituted with an acyl group, or a C₁₋₈ alkyl groupsubstituted with an unsubstituted or substituted heterocyclicoxy group),when n2 is 1 or more and at least one R is a cyano group, a nitro group,a hydroxyl group, a thiol group, a formyl group, a carboxyl group, anunsubstituted or substituted amino group, an unsubstituted orsubstituted C₁₋₈ alkyl group, an unsubstituted or substituted C₂₋₈alkenyl group, an unsubstituted or substituted C₂₋₈ alkynyl group, anunsubstituted or substituted aryl group, an unsubstituted or substitutedheterocyclic group, OR¹, S(O)_(m)R¹, COR¹, or CO₂R¹, or when n2 is 2 ormore and at least two R(s) are halogen atoms, Z represents a hydrogenatom, an amino group, or a group represented by formula: Q³C(═O)NH— (inwhich Q³ represents a hydrogen atom, a C₁₋₈ alkyl group, a C₁₋₈haloalkyl group, a C₂₋₈ alkenyl group, a C₂₋₈ haloalkenyl group, a C₂₋₈alkynyl group, a C₂₋₈ haloalkynyl group, a C₁₋₈ alkoxy group, a C₁₋₈haloalkoxy group, a C₂₋₈ alkenyloxy group, a C₂₋₈ haloalkenyloxy group,a C₂₋₈ alkynyloxy group, a C₂₋₈ haloalkynyloxy group, a C₃₋₈ cycloalkylgroup, a C₃₋₈ cycloalkyloxy group, a C₁₋₈ alkylamino group, a C₁₋₈alkoxy group substituted with an unsubstituted or substituted aminogroup, a C₁₋₈ alkoxy group substituted with a C₃₋₈ cycloalkyl group, anunsubstituted or substituted aralkyloxy group, a C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted heterocyclic group, aC₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈alkoxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted orsubstituted aryloxy group, a C₁₋₈ alkoxy group substituted with anunsubstituted or substituted aralkyloxy group, a C₂₋₈ alkynyloxy groupsubstituted with an unsubstituted or substituted aryl group, a C₁₋₈alkoxy group substituted with an unsubstituted or substituted C₁₋₈alkylthio group, a C₁₋₈ alkoxy group substituted with a substituted orunsubstituted arylthio group, a C₁₋₈ alkoxy group substituted with anunsubstituted or substituted C₁₋₈ alkylsulfinyl group, a C₁₋₈ alkoxygroup substituted with an unsubstituted or substituted arylsulfinylgroup, a C₁₋₈ alkoxy group substituted with an unsubstituted orsubstituted C₁₋₈ alkylsulfonyl group, a C₁₋₈ alkoxy group substitutedwith an unsubstituted or substituted arylsulfonyl group, anunsubstituted or substituted aryloxy group, a C₁₋₈ alkyl groupsubstituted with a carboxyl group, a C₁₋₈ alkyl group substituted withan unsubstituted or substituted amino group, a C₁₋₈ alkyl groupsubstituted with an unsubstituted or substituted aryloxy group, a C₁₋₈alkyl group substituted with an unsubstituted or substituted C₁₋₈alkylthio group, a C₁₋₈ alkyl group substituted with an unsubstituted orsubstituted alkoxy group, an alkyl group substituted with an acyl group,or a C₁₋₈ alkyl group substituted with an unsubstituted or substitutedheterocyclicoxy group), or a thiazoyl group represented by formula (5):

(in which R¹¹ represents a hydrogen atom, a halogen atom, a cyano group,a nitro group, a hydroxyl group, a thiol group, a formyl group, acarboxyl group, an unsubstituted or substituted amino group, anunsubstituted or substituted C₁₋₈ alkyl group, an unsubstituted orsubstituted C₂₋₈ alkenyl group, an unsubstituted or substituted C₂₋₈alkynyl group, an unsubstituted or substituted aryl group, anunsubstituted or substituted heterocyclic group, OR¹, S(O)_(m)R¹, COR¹,or CO₂R¹,R¹ is the same as defined above,when R¹¹ is a hydrogen atom, Z¹¹ represents a group represented byformula: Q′C(═O)NH— (in which Q¹ is the same as defined above),when R¹¹ is a halogen atom, Z¹¹ represents a hydrogen atom, an aminogroup, or a group represented by formula:Q²C(═O)NH— (in which Q² is the same as defined above), and when R¹¹ is acyano group, a nitro group, a hydroxyl group, a thiol group, a formylgroup, a carboxyl group, an unsubstituted or substituted amino group, anunsubstituted or substituted C₁₋₈ alkyl group, an unsubstituted orsubstituted C₂₋₈ alkenyl group, an unsubstituted or substituted C₂₋₈alkynyl group, an unsubstituted or substituted aryl group, anunsubstituted or substituted heterocyclic group, OR¹, S(O)_(m)R¹, COR¹,or CO₂R¹, represents a hydrogen atom, an amino group, or a grouprepresented by formula: Q³C(═O)NH— (in which Q³ is the same as definedabove), and a salt thereof.[2] The tetrazoyloxime derivative according to [1], wherein n1 is 0, orX is halogen atom, and a salt thereof.[3] The tetrazoyloxime derivative according to [1] or [2], wherein Y isa methyl group, and a salt thereof.

According to a second aspect of the present invention, a plant diseasecontrolling agent including the tetrazoyloxime derivative according toany one of [1] to [3] or a salt thereof as an active ingredient isprovided.

Effects of the Invention

According to the present invention, a tetrazoyloxime derivative which isexcellent in a control effect against plant disease injury, or a saltthereof, and a plant disease controlling agent containing the same as anactive ingredient are provided.

BEST MODE FOR CARRYING OUT THE INVENTION

The present invention will be explained in detail by itemizing into 1) atetrazoyloxime derivative and a salt thereof, and 2) a plant diseasecontrolling agent.

1) Tetrazoyloxime Derivative and a Salt Thereof

The first aspect of the present invention is directed to atetrazoyloxime derivative represented by formula (1) shown above, and asalt thereof.

In formula (1) shown above, X represents a halogen atom, a C₁₋₈ alkylgroup, a C₁₋₈ alkoxy group, a cyano group, a C₁₋₈ alkylsulfonyl group, anitro group, a C₁₋₈ haloalkyl group, or an unsubstituted or substitutedaryl group.

Specific examples of the halogen atom for X include a fluorine atom, achlorine atom, a bromine atom, and an iodine atom.

Specific examples of the C₁₋₈ alkyl group include a methyl group, anethyl group, an n-propyl group, an i-propyl group, an n-butyl group, ani-butyl group, an s-butyl group, a t-butyl group, an n-pentyl group, andan n-hexyl group.

Specific examples of the C₁₋₈ alkoxy group include a methoxy group, anethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group,an i-butoxy group, an s-butoxy group, a t-butoxy group, and ann-hexyloxy group.

Specific examples of the C₁₋₈ alkylsulfonyl group include amethylsulfonyl group, an ethylsulfonyl group, an n-propylsulfonyl group,an isopropylsulfonyl group, and a t-butylsulfonyl group.

Specific examples of the C₁₋₈ haloalkyl group include a fluoromethylgroup, a chloromethyl group, a bromomethyl group, a difluoromethylgroup, a dichloromethyl group, a trifluoromethyl group, atrichloromethyl group, a trifluoroethyl group, a pentafluoroethyl group,a 3,3,3,2,2-pentafluoropropyl group, and a2,2,2-trifluoro-1-trifluoromethylethyl group.

An aryl group an unsubstituted or substituted aryl group means amonocyclic or polycyclic aryl group, and the polycyclic aryl groupincludes, in addition to a completely unsaturated group, a partiallyunsaturated group. Specifically, a phenyl group, a 1-naphthyl group, a2-naphthyl group, an azulenyl group, an indanyl group, and a tetralinylgroup are exemplified, and a C₆₋₁₀ aryl group is preferred.

The substituent of the aryl group of the unsubstituted or substitutedaryl group is not particularly limited as long as it is chemicallyacceptable. Specific examples of the substituent include substituentsshown below:

(1) halogen atoms such as a fluorine atom, a chlorine atom, a bromineatom, and an iodine atom,

(2) alkyl groups such as a methyl group, an ethyl group, an n-propylgroup, an i-propyl group, an n-butyl group, an s-butyl group, an i-butylgroup, a t-butyl group, an n-pentyl group, and an n-hexyl group,

(3) cycloalkyl groups such as a cyclopropyl group, a cyclobutyl group, acyclopentyl group, a cyclohexyl group, and a cycloheptyl group,

(4) alkoxy groups such as a methoxy group, an ethoxy group, an n-propoxygroup, an isopropoxy group, an n-butoxy group, an i-butoxy group, ans-butoxy group, and a t-butoxy group,

(5) alkenyl groups such as a vinyl group, a 1-propenyl group, a2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenylgroup, a 1-methyl-2-propenyl group, a 2-methyl-2-propenyl group, a1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenylgroup, a 1-methyl-2-butenyl group, a 2-methyl-2-butenyl group, a1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenylgroup, and a 5-hexenyl group,(6) cycloalkenyl groups such as a 2-cyclopropenyl group, a2-cyclopentenyl group, a 3-cyclohexenyl group, and a 4-cyclooctenylgroup,(7) alkenyloxy groups such as a vinyloxy group, an allyloxy group, a1-propenyloxy group, a 2-butenyloxy group, a(8) alkynyl groups such as ethynyl group, a 1-propynyl group, a2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynylgroup, a 1-methyl-2-propynyl group, a 2-methyl-3-butynyl group, a1-pentynyl group, a 2-pentynyl group, a 3-pentynyl group, a 4-pentynylgroup, a 1-methyl-2-butynyl group, a 2-methyl-3-pentynyl group, a1-hexynyl group, and a 1,1-dimethyl-2-butynyl group,(9) alkynyloxy groups such as an ethynyloxy group and a propargyloxygroup,(10) aryl groups such as a phenyl group, a 1-naphthyl group, and a2-naphthyl group,(11) aryloxy groups such as a phenoxy group and a 1-naphthoxy group,(12) aralkyl groups such as a benzyl group and a phenethyl group,(13) aralkyloxy groups such as a benzyloxy group and a phenethyloxygroup,(14) acyl groups such as a formyl group, an acetyl group, a propionylgroup, a benzoyl group, a cyclohexylcarbonyl group, and a phthaloylgroup,(15) alkoxycarbonyl groups such as a methoxycarbonyl group, anethoxycarbonyl group, an n-propoxycarbonyl group, an isopropoxycarbonylgroup, an n-butoxycarbonyl group, and a t-butoxycarbonyl group,(16) carboxyl groups,(17) hydroxyl groups,(18) haloalkyl groups such as a chloromethyl group, a chloroethyl group,a 1,2-dichloro-n-propyl group, a 1-fluoro-n-butyl group, aperfluoro-n-pentyl group, a haloalkoxy groups such as 2-chloro-n-propoxygroup, a 2,3-dichlorobutoxy group, and a trifluoromethoxy group,(19) haloalkenyl groups such as a 2-chloro-1-propenyl group and a2-fluoro-1-butenyl group,(20) haloalkynyl groups such as a 4,4-dichloro-1-butynyl group, a4-fluoro-1-pentynyl group, and a 5-bromo-2-pentynyl group,(21) haloalkenyloxy groups such as a 2-chloro-1-propenyloxy group and a3-bromo-2-butenyloxy group,(22) haloalkynyl groups such as a 3-chloro-propargyl group and a3-iodo-propargyl group,(23) haloalkynyloxy groups such as a 3-chloro-propargyloxy group and a3-iodo-propargyloxy group,(24) haloaryl groups such as a 4-chlorophenyl group, a 4-fluorophenylgroup, and a 2,4-dichlorophenyl group,(25) haloaryloxy groups such as a 4-fluorophenoxy group and a4-chloro-1-naphthoxy group,(26) halogen-substituted acyl groups such as a chloroacetyl group, atrifluoroacetyl group, a trichloroacetyl group, and a 4-chlorobenzoylgroup,(27) alkoxyalkyl groups such as a methoxymethyl group, an ethoxymethylgroup, a 1-ethoxyethyl group, and a 2-ethoxyethyl group,(28) alkoxyalkoxy groups such as a methoxymethoxy group, anethoxymethoxy group, a 1-ethoxyethoxy group, and a 2-ethoxyethoxy group,(29) cyano groups,(30) isocyano groups,(31) nitro groups,(32) isocyanato groups,(33) cyanato groups,(34) amino groups,(35) alkylamino groups such as a methylamino group, a dimethylaminogroup, and a diethylamino group,(36) arylamino groups such as an anilino group, a naphthylamino group,and an anthranyl amino group,(37) aralkylamino groups such as a benzylamino group and aphenethylamino group,(38) alkylsulfonylamino groups such as a methylsulfonylamino group, anethylsulfonylamino group, an n-propylsulfonylamino group, anisopropylsulfonylamino group, and an n-butylsulfonylamino group,(39) arylsulfonylamino groups such as a phenylsulfonylamino group,(40) heteroarylsulfonylamino groups such as a piperazinylsulfonylaminogroup(41) acylamino groups such as a formylamino group, an acetylamino group,a propanoylamino group, a butyrylamino group, an isopropylcarbonylaminogroup, and a benzoylamino group(42) alkoxycarbonylamino groups such as a methoxycarbonylamino group andan ethoxycarbonylamino group,(43) haloalkylsulfonylamino groups such as a fluoromethylsulfonylaminogroup, a chloromethylsulfonylamino group, a bromomethylsulfonylaminogroup, a difluoromethylsulfonylamino group, adichloromethylsulfonylamino group, a 1,1-difluoroethylsulfonylaminogroup, a trifluoromethylsulfonylamino group, a2,2,2-trifluoroethylsulfonylamino group, and a pentafluorosulfonylaminogroup,(44) bis(alkylsulfonyl)amino groups such as a bis(methylsulfonyl)aminogroup, a bis(ethylsulfonyl)amino group, an(ethylsulfonyl)(methylsulfonyl)amino group, a bis(n-propylsulfonyl)aminogroup, a bis(isopropylsulfonyl)amino group, a bis(n-butylsulfonyl)aminogroup, and a bis(t-butylsulfonyl)amino group,(45) bis(haloalkylsulfonyl)amino groups such as abis(fluoromethylsulfonyl)amino group, a bis(chloromethylsulfonyl)aminogroup, a bis(bromomethylsulfonyl)amino group, abis(dichloromethylsulfonyl)amino group, abis(1,1-difluoroethylsulfonyl)amino group, abis(trifluoromethylsulfonyl)amino group, abis(2,2,2-trifluoroethyl)amino group, and abis(pentafluoroethylsulfonyl)amino group,(46) unsubstituted or substituted hydrazino groups such as a hydrazinogroup, an N′-phenylhydrazino group, an N′-methoxycarbonylhydrazinogroup, an N′-acetylhydrazino group, and an N′-methylhydrazino group,(47) unsubstituted or substituted aminocarbonyl groups such as anaminocarbonyl group, a dimethylaminocarbonyl group, aphenylaminocarbonyl group, and an N-phenyl-N-methylcarbonyl group,(48) unsubstituted or substituted hydrazinocarbonyl groups such as ahydrazinocarbonyl group, an N′-methylhydrazinocarbonyl group, and anN′-phenylhydrazinocarbonyl group,(49) unsubstituted or substituted iminoalkyl groups such as anN-methyliminomethyl group, a 1-N-phenyliminoethyl group, anN-hydroxyiminomethyl group, and an N-methoxyiminomethyl group,(50) thiol groups,(51) isothiocyanato groups,(52) thiocyanato groups,(53) alkylthio groups such as a methylthio group, an ethylthio group, ann-propylthio group, an isopropylthio group, an n-butylthio group, anisobutylthio group, an s-butylthio group, and a t-butylthio group,(54) alkenylthio groups such as vinylthio group, an allylthio group,(55) alkynylthio groups such as an ethynylthio group and a propargylthiogroup,(56) arylthio groups such as a phenylthio group and a naphthylthiogroup,(57) heteroarylthio groups such as 2-piperidylthio group, a3-pyridazylthio group,(58) aralkylthio groups such as a benzylthio group and a phenethylthiogroup,(59) heteroarylalkylthio groups such as a 2-pyridylmethylthio group anda 2-furylmethylthio group,(60) alkylthiocarbonyl groups such as a methylthiocarbonyl group, anethylthiocarbonyl group, an n-propylthiocarbonyl group, anisopropylthiocarbonyl group, an n-butylthiocarbonyl group, anisobutylthiocarbonyl group, an s-butylthiocarbonyl group, and at-butylthiocarbonyl group,(61) alkylthioalkyl groups such as a methylthiomethyl group and a1-methylthioethyl group,(62) arylthioalkyl groups such as a phenylthiomethyl group and a1-phenylthioethyl group,(63) alkylthioalkoxy groups such as a methylthiomethoxy group and a1-methylthioethoxy group,(64) arylthioalkoxy groups such as a phenylthiomethoxy group and a1-phenylthioethoxy group,(65) alkylsulfinyl groups such as a methylsulfinyl group, anethylsulfinyl group, and a t-butylsulfenyl group,(66) alkenylsulfinyl groups such as an allylsulfinyl group, (67)alkynylsulfinyl groups such as a propargylsulfinyl group,(68) arylsulfinyl groups such as a phenylsulfinyl group,(69) heteroarylsulfinyl groups such as a 2-pyridylsulfinyl group and a3-pyridylsulfinyl group,(70) aralkylsulfinyl groups such as a benzylsulfinyl group and aphenethylsulfinyl group,(71) heteroarylalkylsulfenyl groups such as a 2-pyridylmethylsulfinylgroup and a 3-pyridylmethylsulfinyl group,(72) alkylsulfonyl groups such as a methylsulfonyl group, anethylsulfonyl group, and a t-butylsulfonyl group,(73) alkenylsulfonyl groups such as an allylsulfonyl group,(74) alkynylsulfonyl groups such as a propargylsulfonyl group,(75) arylsulfonyl groups such as a phenylsulfonyl group,(76) heteroarylsulfonyl groups such as 2-pyridylsulfonyl group and a3-pyridylsulfonyl group,(77) aralkylsulfonyl groups such as a benzylsulfonyl group and aphenethylsulfonyl group,(78) heteroarylalkylsulfonyl groups such as a 2-pyridylmethylsulfonylgroup and a 3-pyridylmethylsulfonyl group,(79) unsaturated 5-membered heterocyclic groups such as a furan-2-ylgroup, a furan-3-yl group, a thiophen-2-yl group, a thiophen-3-yl group,a pyrrol-2-yl group, a pyrrol-3-yl group, an oxazol-2-yl group, anoxazol-4-yl group, an oxazol-5-yl group, a thiazol-2-yl group, athiazol-4-yl group, a thiazol-5-yl group, an isooxazol-3-yl group, anisooxazol-4-yl group, an isooxazol-5-yl group, an isothiazol-3-yl group,an isothiazol-4-yl group, an isothiazol-5-yl group, an imidazol-2-ylgroup, an imidazol-4-yl group, an imidazol-5-yl group, a pyrazol-3-ylgroup, a pyrazol-4-yl group, a pyrazol-5-yl group, a1,3,4-oxadiazol-2-yl group, a 1,3,4-thiadiazol-2-yl group, a1,2,3-triazol-4-yl group, a 1,2,4-triazol-3-yl group, and a1,2,4-triazol-5-yl group,(80) unsaturated 6-membered heterocyclic groups such as a pyridin-2-ylgroup, a pyridin-3-yl group, a pyridin-4-yl group, a 5-chloro-3-pyridylgroup, a 3-trifluoromethyl-2-pyridyl group, a pyridazin-3-yl group, apyridazin-4-yl group, a pyrazin-2-yl group, a pyrimidin-5-yl group, a1,3,5-triazin-2-yl group, and a 1,2,4-triazin-3-yl group,(81) saturated or partially unsaturated heterocyclic groups such as atetrahydrofuran-2-yl group, a tetrahydropyran-4-yl group, apiperidin-3-yl group, a pyrrolidin-2-yl group, a morpholino group, apiperidino group, an N-methylpiperazino group, and an oxazolin-2-ylgroup,(82) heterocyclicoxy groups such as a 2-pyridyloxy group and a3-isooxazolyloxy group,(83) heteroarylalkyl groups such as a 2-pyridylmethyl group and a3-pyridylmethyl group, and(84) heteroarylalkoxy groups such as a 2-pyridylmethoxy group and a3-pyridylmethoxy group.

These substituents exemplified in (1) to (84) can also be substitutedwith those exemplified in (1) to (84).

Specific examples of the substituted aryl group include a 4-fluorophenylgroup, a 2,4-dichlorophenyl group, a 3,5-dichlorophenyl group, a2,6-difluorophenyl group, a 4-methoxyphenyl group, and a3,4-dimethoxyphenyl group.

Among these, X is preferably a halogen atom.

n1 represents any one of integers of 0 to 5, and preferably any one ofintegers of 0 to 3.

When n1 is 2 or more, X(s) may be the same or different with each other.

A represents a tetrazoyl group represented by formula (2) or formula(3), and preferably formula (2).

In formulas (2) and (3), Y represents a C₁₋₈ alkyl group. Examples ofthe C₁₋₈ alkyl group include a methyl group, an ethyl group, an n-propylgroup, an i-propyl group, an n-butyl group, an i-butyl group, an s-butylgroup, a t-butyl group, an n-pentyl group, and an n-hexyl group.

Among these, Y is preferably a C₁₋₃ alkyl group, and particularlypreferably a methyl group.

Het represents a pyridyl group represented by formula (4) or a thiazolylgroup represented by formula (5).

In formulas (4) and (5), R represents a halogen atom, a cyano group, anitro group, a hydroxyl group, a thiol group, a formyl group, a carboxylgroup, an unsubstituted or substituted amino group, an unsubstituted orsubstituted C₁₋₈ alkyl group, an unsubstituted or substituted C₂₋₈alkenyl group, an unsubstituted or substituted C₂₋₈ alkynyl group, anunsubstituted or substituted aryl group, an unsubstituted or substitutedheterocyclic group, OR¹, S(O)_(m)R¹, COR¹, or CO₂R¹.

Specific examples of the halogen atom, the C₁₋₈ alkyl group of theunsubstituted or substituted C₁₋₈ alkyl group, and the aryl group of theunsubstituted or substituted aryl group for R are the same as those forX.

Specific examples of the C₂₋₈ alkenyl group of the unsubstituted orsubstituted C₂₋₈ alkenyl group for R include a vinyl group, a 1-propenylgroup, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a3-butenyl group, a 1-methyl-2-propenyl group, a 2-methyl-2-propenylgroup, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a4-pentenyl group, a 1-methyl-2-butenyl group, a 2-methyl-2-butenylgroup, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a4-hexenyl group, and a 5-hexenyl group.

Specific examples of the C₂₋₈ alkynyl group of the unsubstituted orsubstituted C₂₋₈ alkynyl group for R include an ethynyl group, a1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynylgroup, a 3-butynyl group, a 1-methyl-2-propynyl group, a2-methyl-3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a3-pentynyl group, a 4-pentynyl group, a 1-methyl-2-butynyl group, a2-methyl-3-pentynyl group, a 1-hexynyl group, and a1,1-dimethyl-2-butynyl group.

Specific examples of the heterocyclic group of the unsubstituted orsubstituted heterocyclic group for R include unsaturated 5-memberedheterocyclic groups such as a furan-2-yl group, a furan-3-yl group, athiophen-2-yl group, a thiophen-3-yl group, a pyrrol-2-yl group, apyrrol-3-yl group, an oxazol-2-yl group, an oxazol-4-yl group, anoxazol-5-yl group, a thiazol-2-yl group, a thiazol-4-yl group, athiazol-5-yl group, an isooxazol-3-yl group, an isooxazol-4-yl group, anisooxazol-5-yl group, an isothiazol-3-yl group, an isothiazol-4-ylgroup, an isothiazol-5-yl group, an imidazol-2-yl group, animidazol-4-yl group, an imidazol-5-yl group, a pyrazol-3-yl group, apyrazol-4-yl group, a pyrazol-5-yl group, a 1,3,4-oxadiazol-2-yl group,a 1,3,4-thiadiazol-2-yl group, a 1,2,3-triazol-4-yl group, a1,2,4-triazol-3-yl group, and a 1,2,4-triazol-5-yl group; unsaturated6-membered heterocyclic groups such as a pyridin-2-yl group, apyridin-3-yl group, a pyridin-4-yl group, a 5-chloro-3-pyridyl group, a3-trifluoromethyl-2-pyridyl group, a pyridazin-3-yl group, apyridazin-4-yl group, a pyrazin-2-yl group, a pyrimidin-5-yl group, a1,3,5-triazin-2-yl group, and a 1,2,4-triazin-3-yl group; and saturatedor partially unsaturated heterocyclic groups such as atetrahydrofuran-2-yl group, a tetrahydropyran-4-yl group, apiperidin-3-yl group, a pyrrolidin-2-yl group, a morpholino group, apiperidino group, a piperazino group, an N-methylpiperazino group, anaziridino group, an azetidino group, a pyrrolidino group, a morpholinogroup, and an oxazolin-2-yl group.

As the substituent of the amino group, the C₁₋₈ alkyl group, the C₂₋₈alkenyl group, the C₂₋₈ alkynyl group, the aryl group, and theheteroaryl group, for example, the same substituents as those of thearyl group for X can be exemplified in a chemically acceptable range.

Specific examples of the substituted amino group include a methylaminogroup, a dimethylamino group, a methylethylamino group, a diethylaminogroup, a t-butoxycarbonylmethylamino group, a t-butoxycarbonylaminogroup, an acetylmethylamino group, an acetylethylamino group, and abenzoylmethylamino group.

Specific examples of the substituted C₁₋₈ alkyl group include achloromethyl group, a methoxymethyl group, a methylthiomethyl group, amethylsulfonylmethyl group, a dimethylaminomethyl group, atrichloromethyl group, a trifluoromethyl group, and a 2-chloroethylgroup.

Specific examples of the substituted C₂₋₈ alkenyl group include a2-chloroethenyl group, a 2-fluoroethenyl group, a3,3,3-trifluoro-1-pentenyl group, a 1,2,2-trifluoroethenyl group, a2,3,3-trifluoro-2-propenyl group, a 2,3,3-triiodo-2-propenyl group, anda 2-methoxyethenyl group.

Specific examples of the substituted C₂₋₈ alkynyl group include a2-chloroethynyl group, a 2-fluoroethynyl group, a 3-fluoro-1-propynylgroup, a 3,3,3-trifluoro-1-propynyl group, a 3-fluoro-2-propynyl group,and a 3-iodo-2-propynyl group.

Specific examples of the substituted aryl group include a 4-chlorophenylgroup, a 2,4-dichlorophenyl group, a 3,4-dichlorophenyl group, a4-trifluoromethylphenyl group, a 4-methoxyphenyl group, a3,4-dimethoxyphenyl group, a 3,4-methylenedioxyphenyl group, a4-trifluoromethoxyphenyl group, and a 4-methoxy-1-naphthyl group.

Specific examples of the substituted heterocyclic group include a3-trifluoromethylpyridin-2-yl group, a 4-trifluoromethoxy-2-pyridylgroup, a 3-methyl-1-pyrazolyl group, a 4-trifluoromethyl-1-imidazolylgroup, and a 3,4-difluoropyrrolidino group.

R¹ of OR¹, COR¹, S(O)_(m)R¹, and CO₂R¹ for R represents an unsubstitutedor substituted amino group, an unsubstituted or substituted C₁₋₈ alkylgroup, an unsubstituted or substituted C₃₋₈ cycloalkyl group, anunsubstituted or substituted C₂₋₈ alkenyl group, an unsubstituted orsubstituted C₂₋₈ alkynyl group, an unsubstituted or substituted arylgroup, or an unsubstituted or substituted heterocyclic group.

As specific examples of the unsubstituted or substituted amino group,the unsubstituted or substituted C₁₋₈ alkyl group, the unsubstituted orsubstituted C₂₋₈ alkenyl group, the unsubstituted or substituted C₂₋₈alkynyl group, the unsubstituted or substituted aryl group, and theunsubstituted or substituted heterocyclic group, for example, the samegroups as those for R can be exemplified.

Specific examples of the C₃₋₈ cycloalkyl group of the unsubstituted orsubstituted C₃₋₈ cycloalkyl group include a cyclopropyl group, acyclobutyl group, a cyclopentyl group, a cyclohexyl group, and acycloheptyl group.

Specific examples of the substituted C₃₋₈ cycloalkyl group include a2-methylcyclopropyl group, a 2-chloro-cyclopropyl group, a2-trifluoromethylcyclobutyl group, a 2,3,4-trifluorocyclopentyl group,and a 2,2,3,3-tetrafluorocyclopropyl group.

Specific examples of OR¹ include a methoxy group, an ethoxy group, ann-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxygroup, an i-butoxy group, a t-butoxy group, a methoxymethoxy group, anethoxymethoxy group, a 2-methoxyethoxy group, a 1-ethoxyethoxy group, avinyloxy group, a 1-propenyloxy group, a 2-propenyloxy group, anethynyloxy group, a 1-propynyloxy group, a 2-propynyloxy group, anaminooxy group, a methylaminooxy group, a diethylaminooxy group, amethoxycarbonylaminooxy group, a phenoxy group, a trichloromethoxygroup, a trifluoromethoxy group, a difluoromethoxy group, a2,2,2-trifluoroethoxy group, a pentafluoroethoxy group, and a2-fluoroethoxy group.

Specific examples of COR¹ include an acetyl group, a benzoyl group, apropanoyl group, an i-propylcarbonyl group, a t-butylcarbonyl group, acyclopropylcarbonyl group, a cyclobutylcarbonyl group, acyclopentylcarbonyl group, a vinylcarbonyl group, a 1-propenylcarbonylgroup, a 2-propenylcarbonyl group, an i-propenylcarbonyl group, a1-propynylcarbonyl group, a 2-propynylcarbonyl group, a3-butenylcarbonyl group, a methylaminocarbonyl group, adimethylaminocarbonyl group, an N-methyl-N-ethylaminocarbonyl group, anaziridinocarbonyl group, an azetidinocarbonyl group, apyrrolidinocarbonyl group, a piperidinocarbonyl group, amorpholinocarbonyl group, a piperazinocarbonyl group, and anN-methylpiperazinocarbonyl group.

Specific examples of CO₂R¹ include a methoxycarbonyl group, atrifluoromethoxycarbonyl group, a 1-pentenyloxycarbonyl group, a2-propynyloxycarbonyl group, and a phenoxycarbonyl group.

Specific examples of S(O)_(m)R¹ for R include a dimethylaminothio group,a chloromethylthio group, a 3-butenylthio group, an ethynylthio group, a3-methylphenylthio group, a methylsulfinyl group, an ethylsulfinylgroup, a 1-butenylsulfinyl group, an n-hexylsulfinyl group, a2,3-dimethylphenylsulfinyl group, a methylsulfonyl group, adimethylaminosulfonyl group, an N-ethyl-N-methylaminosulfonyl group, ann-hexylsulfonyl group, a 2-methyl-2-butenylsulfonyl group, a2-propynylsulfonyl group, a 2-naphthylsulfonyl group, a phenylsulfonylgroup, a 2-nitrophenylsulfonyl group, and a p-tolylsulfonyl group.

Among these, a halogen atom, an unsubstituted or substituted aminogroup, a C₁₋₈ alkyl group, OR₁, and SR₁ are preferable, and anunsubstituted or substituted amino group, a C₁₋₈ alkyl group, OR¹, andSR₁ are more preferable.

An amino group and a dialkylamino group can be preferably exemplified asthe unsubstituted or substituted amino group, a C₁₋₄ alkyl group can bepreferably exemplified as the C₁₋₈ alkyl group, a C₁₋₄ alkoxy group canbe preferably exemplified as OR₁, and a C₁₋₄ alkylthio group can bepreferably exemplified as SR₁.

m represents any one of integers of 0 to 2.

n2 represents any one of integers of 0 to 3.

When n2 is 2 or more, plural R(s) may be the same or different from eachother.

When n2 is 0, Z represents a group represented by formula: Q¹C(═O)NH—(in which Q¹ represents a C₁₋₈ haloalkyl group, a C₂₋₈ haloalkenylgroup, a C₂₋₈ alkynyl group, a C₂₋₈ haloalkynyl group, a C₁₋₈ haloalkoxygroup, a C₂₋₈ alkenyloxy group, a C₂₋₈ haloalkenyloxy group, a C₂₋₈alkynyloxy group, a C₂₋₈ haloalkynyloxy group, a C₁₋₈ alkoxy groupsubstituted with an alkoxycarbonylamino group, a C₁₋₈ alkoxy groupsubstituted with a C₃₋₈ cycloalkyl group, a C₁₋₈ branched alkoxy groupsubstituted with an unsubstituted aryl group, a C₁₋₈ alkoxy groupsubstituted with a substituted aryl group, a C₁₋₈ alkoxy groupsubstituted with a substituted or unsubstituted heterocyclic group, aC₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈alkoxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted orsubstituted aryloxy group, a C₁₋₈ alkoxy group substituted with anunsubstituted or substituted aralkyloxy group, a C₂₋₈ alkynyloxy groupsubstituted with an unsubstituted or substituted aryl group, a C₁₋₈alkoxy group substituted with an unsubstituted or substituted C₁₋₈alkylthio group, a C₁₋₈ alkoxy group substituted with an unsubstitutedor substituted arylthio group, a C₁₋₈ alkoxy group substituted with anunsubstituted or substituted C₁₋₈ alkylsulfinyl group, a C₁₋₈ alkoxygroup substituted with an unsubstituted or substituted arylsulfinylgroup, a C₁₋₈ alkoxy group substituted with an unsubstituted orsubstituted C₁₋₈ alkylsulfonyl group, a C₁₋₈ alkoxy group substitutedwith an unsubstituted or substituted arylsulfonyl group, a C₁₋₈ alkoxygroup substituted with an amino group which is unsubstituted orsubstituted with an (unsubstituted or substituted alkyl group), a C₁₋₈alkoxy group which is substituted with an amino group substituted withan (unsubstituted or substituted aralkyl group), an unsubstituted orsubstituted aryloxy group, a C₁₋₈ alkyl group substituted with acarboxyl group, a C₁₋₈ alkyl group substituted with an amino group whichis unsubstituted or substituted with an (unsubstituted or substitutedaralkyl group), a C₁₋₈ alkyl group substituted with an amino group whichis substituted with an (unsubstituted or substituted alkyl group), aC₁₋₈ alkyl group substituted with an unsubstituted or substitutedaryloxy group, a C₁₋₈ alkyl group substituted with an acyl group, or aC₁₋₈ alkyl group substituted with an unsubstituted or substitutedheterocyclic group).

Specific examples of the C₁₋₈ haloalkyl group for Q¹ include achloromethyl group, a chloroethyl group, a 1,2-dichloro-n-propyl group,a 1-fluoro-n-butyl group, and a perfluoro-n-pentyl group.

Specific examples of the C₂₋₈ haloalkenyl group for Q¹ include a1-chlorovinyl group, a 2-bromovinyl group, a 3-fluoroallyl group, and a2-fluorocrotyl group.

Specific examples of the C₂₋₈ alkynyl group for Q¹ include an ethynylgroup, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a2-butynyl group, a 3-butynyl group, a 1-methyl-2-propynyl group, a2-methyl-3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a3-pentynyl group, a 4-pentynyl group, a 1-methyl-2-butynyl group, a2-methyl-3-pentynyl group, a 1-hexynyl group, and a1,1-dimethyl-2-butynyl group.

Specific examples of the C₂₋₈ haloalkynyl group for Q¹ include achloroethynyl group, a bromoethynyl group, an iodoethynyl group, a3-chloro-1-propynyl group, a 3-chloro-1-butynyl group, and a3-bromo-1-butynyl group.

Specific examples of the C₁₋₈ haloalkoxy group for Q¹ include achloromethoxy group, a difluoromethoxy group, a trifluoromethoxy group,a 1,1-difluoroethoxy group, and a hexafluoroethoxy group.

Specific examples of the C₂₋₈ alkenyloxy group for Q¹ include anethenyloxy group, a 1-propenyloxy group, a 1-methylvinyloxy group, anallyloxy group, a 1-methylallyloxy group, and a 2-butenyloxy group.

Specific examples of the C₂₋₈ haloalkenyloxy group for Q¹ include a3-chloro-2-propenyloxy group, a 3,3-dichloro-2-propenyloxy group, a4-chloro-2-butenyloxy group, a 4,4-dichloro-3-butenyloxy group, and a4,4-difluoro-3-butenyloxy group.

Specific examples of the C₂₋₈ alkynyloxy group for Q¹ include a2-propynyloxy group, a 2-butynyloxy group, and a 1-methyl-2-propynyloxygroup.

Specific examples of the C₂₋₈ haloalkynyloxy group for Q¹ include a2-chloroethynyloxy group, a 3-chloro-2-propynyloxy group, and a3-fluoro-2-propynyloxy group.

Specific examples of the alkoxycarbonyl group of the C₁₋₈ alkoxy groupsubstituted with an alkoxycarbonylamino group for Q¹ include amethoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonylgroup, an isopropoxycarbonyl group, an n-butoxycarbonyl group, and at-butoxycarbonyl group. As the C₁₋₈ alkoxy group, for example, the samealkoxy groups as those for X can be exemplified. Hereinafter, specificexamples of the C₁₋₈ alkoxy group are the same specific examples.Specific examples of the C₁₋₈ alkoxy group substituted with analkoxycarbonylamino group include an N-methoxycarbonylaminomethoxygroup, an N-t-butoxycarbonylaminomethoxy group, a2-(N-ethoxycarbonylamino)ethoxy group, and a2-(N-t-butoxycarbonyl-N-benzylamino) ethoxy group.

Specific examples of the C₃₋₈ cycloalkyl group of the C₁₋₈ alkoxy groupsubstituted with a C₃₋₈ cycloalkyl group for Q¹ include a cyclopropylgroup, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, anda cycloheptyl group. Specific examples of the C₁₋₈ alkoxy groupsubstituted with a C₃₋₈ cycloalkyl group include a cyclopropylmethoxygroup, a 1-cyclopropyl-ethoxy group, a cyclohexylmethoxy group, and a2-cyclohexyl-ethoxy group.

Specific examples of the C₁₋₈ branched alkoxy group substituted with anunsubstituted aryl group include a 1-phenylethoxy group, a1-phenyl-1-methylethoxy group, and a 2-phenyl-1-methylethoxy group.

As the aryl group of the C₁₋₈ alkoxy group substuituted with asubstituted aryl group for Q¹, for example, the same aryl groups asthose for X can be exemplified. The substituent of the aryl group is notparticularly limited and, for example, the same substituents as those ofthe aryl group for X can be exemplified in a chemically acceptablerange. Specific examples of the C₁₋₈ alkoxy group substituted with asubstituted aryl group include a 2-methylphenylmethoxy group, a3-methylphenylmethoxy group, a 4-chlorophenylmethoxy group, a1-(4-chlorophenyl)ethoxy group, a 3-chlorophenylmethoxy group, a2-methoxyphenylmethoxy group, a 3-methoxyphenylmethoxy group, a4-methylsulfonylphenylmethoxy group, and a 3-phenylphenylmethoxy group.

As the heterocyclic group of the C₁₋₈ alkoxy group substuituted with anunsubstituted or substituted heterocyclic group for Q¹, for example, thesame heterocyclic groups as those for R can be exemplified. Thesubstituent of the heterocycle is not particularly limited and, forexample, the same substituents as those of the aryl group for X can beexemplified in a chemically acceptable range. Specific examples of theC₁₋₈ alkoxy group substituted with an unsubstituted or substitutedheterocyclic group include a 2-pyridylmethoxy group, a6-methylpyridin-2-ylmethoxy group, a 4-pyridylmethoxy group, a1-(4-pyridyl)-1-methylethoxy group, a 2-oxazolylmethoxy group, and a2-benzoxazolylmethoxy group.

The substituent of the C₁₋₈ alkoxy group substituted with anunsubstituted or substituted C₁₋₈ alkoxy group for Q¹ is notparticularly limited and, for example, the same substituents as those ofthe aryl group for X can be exemplified in a chemically acceptablerange. Specific examples of the C₁₋₈ alkoxy group substituted with anunsubstituted or substituted C₁₋₈ alkoxy group include a methoxymethoxygroup, an ethoxymethoxy group, a 2-isopropoxyethoxy group, a2-(methoxyethoxy)ethoxy group, a 2-trifluoromethoxyethoxy group, and a2-pentafluoroethoxyethoxy group.

Specific examples of the aryloxy group of the C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted aryloxy group for Q¹include a phenoxy group and a 1-naphthoxy group. The substituent of thearyloxy group is not particularly limited and, for example, the samesubstituents as those of the aryl group for X can be exemplified in achemically acceptable range. Specific examples of the C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted aryloxy group include aphenoxymethoxy group, a 2-phenoxyethoxy group, a2-(4-chlorophenoxy)ethoxy group, and a 2-(4-methoxyphenoxy)ethoxy group.

As the aralkyloxy group of the C₁₋₈ alkoxy group substuituted with anunsubstituted or substituted aralkyloxy group for Q′, for example, abenzyloxy group and a phenethyloxy group can be exemplified. Thesubstituent thereof is not particularly limited and, for example, thesame substituents as those of the aryl group for X can be exemplified ina chemically acceptable range. Specific examples of the C₁₋₈ alkoxygroup substituted with an unsubstituted or substituted aralkyloxy groupinclude a benzyloxymethoxy group, a 2-benzyloxyethoxy group, aphenethyloxymethoxy group, and a (4-chlorophenylmethoxy)methoxy group.

As the aryl group of the C₂₋₈ alkynyloxy group substuituted with anunsubstituted or substituted aryl group for Q′, for example, the samearyl groups as those for X can be exemplified. As the C₂₋₈ alkynyloxygroup, for example, the same alkynyl groups as those for R can beexemplified. The substituent of the aryl group is not particularlylimited and, for example, the same substituents as those of the arylgroup for X can be exemplified in a chemically acceptable range.Specific examples of the C₂₋₈ alkynyloxy group substituted with anunsubstituted or substituted aryl group include a 3-phenyl-2-propynyloxygroup, a 1-phenyl-2-propynyloxy group, and a3-phenyl-1,1-dimethyl-2-propynyloxy group.

Specific examples of the alkylthio group of the C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted C₁₋₈ alkylthio groupfor Q¹ include a methylthio group, an ethylthio group, an n-propylthiogroup, an isopropylthio group, an n-butylthio group, an isobutylthiogroup, an s-butylthio group, and a t-butylthio group. The substituentthereof is not particularly limited and, for example, the samesubstituents as those of the aryl group for X can be exemplified in achemically acceptable range. Specific examples of the C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted C₁₋₈ alkylthio groupinclude a methylthiomethoxy group, a methylthio-n-butoxy group, and a1-methylthioethoxy group.

Specific examples of the arylthio group of the C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted arylthio group for Q¹include a phenylthio group and a naphthylthio group. The substituentthereof is not particularly limited and, for example, the samesubstituents as those of the aryl group for X can be exemplified in achemically acceptable range. Specific examples of the C₁₋₈ alkoxy groupsubstituted with a substituted or unsubstituted arylthio group include aphenylthiomethoxy group, a 2-phenylthioethoxy group, anaphthylthiomethoxy group, and a 1-phenylthioethoxy group.

Specific examples of the alkylsulfinyl group of the C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted C₁₋₈ alkylsulfinylgroup for Q¹ include a methylsulfinyl group, an ethylsulfinyl group, anda t-butylsulfinyl group. The substituent thereof is not particularlylimited and, for example, the same substituents as those of the arylgroup for X can be exemplified in a chemically acceptable range.Specific examples of the C₁₋₈ alkoxy group substituted with anunsubstituted or substituted C₁₋₈alkylsulfinyl group include amethylsulfinylmethoxy group, a methylsulfinyl-n-butoxy group, and a1-methylsulfinylethoxy group.

Specific examples of the arylsulfinyl group of the C₁₋₈ alkoxy groupsubstuituted with an unsubstituted or substituted arylsulfinyl group forQ¹ include a phenylsulfenyl group. The substituent thereof is notparticularly limited and, for example, the same substituents as those ofthe aryl group for X can be exemplified in a chemically acceptablerange. Specific examples of the C₁₋₈ alkoxy group substituted with anunsubstituted or substituted arylsulfinyl group include aphenylsulfinylmethoxy group, a 2-phenylsulfinylethoxy group, anaphthylsulfinylmethoxy group, and a 1-phenylsulfenylethoxy group.

Specific examples of the alkylsulfonyl group of the C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted C₁₋₈ alkylsulfonylgroup for Q¹ include a methylsulfonyl group, an ethylsulfonyl group, anda t-butylsulfonyl group. The substituent thereof is not particularlylimited and, for example, the same substituents as those of the arylgroup for X can be exemplified in a chemically acceptable range.Specific examples of the C₁₋₈ alkoxy group substituted with anunsubstituted or substituted C₁₋₈ alkylsulfonyl group include amethylsulfonylmethoxy group, a methylsulfonyl-n-butoxy group, and a1-methylsulfonylethoxy group.

Specific examples of the arylsulfonyl group of the C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted arylsulfonyl group forQ¹ include a phenylsulfonyl group. The substituent thereof is notparticularly limited and, for example, the same substituents as those ofthe aryl group for X can be exemplified in a chemically acceptablerange. Specific examples of the C₁₋₈ alkoxy group substituted with anunsubstituted or substituted arylsulfonyl group include aphenylsulfonylmethoxy group, a 2-phenylsulfonylethoxy group, anaphthylsulfonylmethoxy group, and a 1-phenylsulfonylethoxy group.

Specific examples of the aralkyl group of the C₁₋₈ alkoxy groupsubstituted with an amino group which is unsubstituted or substitutedwith an (unsubstituted or substituted aralkyl group) for Q¹ include abenzyl group, a phenethyl group, and a 1-naphthylmethyl group. Thesubstituent thereof is not particularly limited and, for example, thesame substituents as those of the aryl group for X can be exemplified ina chemically acceptable range. Specific examples of the C₁₋₈ alkoxygroup substituted with an amino group which is unsubstituted orsubstituted with an (unsubstituted or substituted aralkyl group) includean aminomethoxy group, a 3-aminopropoxy group, a 6-aminohexyloxy group,a 1-aminoethoxy group, benzylaminomethoxy group, anN-benzyl-N-methylaminomethoxy group, and anN-benzyl-N-methoxycarbonylaminomethoxy group.

As the alkyl group of the C₁₋₈ alkoxy group which is substituted with anamino group substituted with an (unsubstituted or substituted alkylgroup) for Q′, for example, the same alkyl groups as those for X can beexemplified. The substituent thereof is not particularly limited and,for example, the same substituents as those of the aryl group for X canbe exemplified in a chemically acceptable range. Specific examples ofthe C₁₋₈ alkoxy group which is substituted with an amino groupsubstituted with an (unsubstituted or substituted alkyl group) include amethylaminomethoxy group, a 3-methylaminopropoxy group, a6-methylaminohexyloxy group, a 1-methylaminoethoxy group, adimethylaminomethoxy group, a 2-ethylaminoethoxy group, and anN-methyl-N-methoxycarbonylaminomethoxy group.

The substituent of the unsubstituted or substituted aryloxy group for Q¹is not particularly limited, and the same substituents as those of thearyl group for X can be exemplified in a chemically acceptable range.Specific examples of the unsubstituted or substituted aryloxy groupinclude a phenoxy group, a naphthyloxy group, a 4-chlorophenoxy group, a4-methoxyphenoxy group, a 2,4-dichlorophenoxy group, and a2-trifluoromethylphenoxy group.

As the C₁₋₈ alkyl group of the C₁₋₈ alkyl group substituted with acarboxyl group for Q¹, for example, the same substituents as those ofthe alkyl group for X can be exemplified. Hereinafter, specific examplesof the C₁₋₈ alkoxy group are the same specific examples. Specificexamples of the C₁₋₈ alkyl group substituted with a carboxyl groupinclude a 2-carboxyethyl group and a 6-carboxyhexyl group.

Specific examples of the aralkyl group of the C₁₋₈ alkyl groupsubstituted with an amino group which is unsubstituted or substitutedwith an (unsubstituted or substituted aralkyl group) for Q¹ include abenzyl group, a phenethyl group, and a 1-naphthylmethyl group. Thesubstituent thereof is not particularly limited and, for example, thesame substituents as those of the aryl group for X can be exemplified ina chemically acceptable range. Specific examples of the C₁₋₈ alkyl groupsubstituted with an amino group which is unsubstituted or substitutedwith an (unsubstituted or substituted aralkyl group) include anaminomethyl group, a 3-aminopropyl group, a 6-aminohexyl group, a1-aminoethyl group, a benzylaminomethyl group, anN-benzyl-N-methylaminomethyl group, and anN-benzyl-N-methoxycarbonylaminomethyl group.

As the alkyl group of the C₁₋₈ alkyl group which is substituted with anamino group substituted with an (unsubstituted or substituted alkylgroup) for Q¹, for example, the same alkyl groups as those for X can beexemplified. The substituent thereof is not particularly limited and,for example, the same substituents as those of the aryl group for X canbe exemplified in a chemically acceptable range. Specific examples ofthe C₁₋₈ alkyl group which is substituted with an amino groupsubstituted with an (unsubstituted or substituted alkyl group) include amethylaminomethyl group, a 3-methylaminopropyl group, a6-methylaminohexyl group, a 1-methylaminoethyl group, adimethylaminomethyl group, a 2-ethylaminoethyl group, and anN-methyl-N-methoxycarbonylaminomethyl group.

Specific examples of the aryloxy group of the C₁₋₈ alkyl groupsubstituted with an unsubstituted or substituted aryloxy group for Q¹include a phenoxy group and a naphthyloxy group. The substituent thereofis not particularly limited and, for example, the same substituents asthose of the aryl group for X can be exemplified in a chemicallyacceptable range. Specific examples of the C₁₋₈ alkyl group substitutedwith an unsubstituted or substituted aryloxy group include aphenoxymethyl group, a naphthyloxymethyl group, a 2-phenoxyethyl group,and a 1-phenoxyethyl group.

Specific examples of the acyl group of the C₁₋₈ alkyl group substitutedwith an acyl group for Q¹ include a formyl group, an acetyl group, apropionyl group, a benzoyl group, a cyclohexylcarbonyl group, and aphthaloyl group. Specific examples of the acyl group of the C₁₋₈ alkylgroup substituted with an acyl group include a 4-acetyl-n-butyl group,an acetylmethyl group, a 1-acetylethyl group, and a 3-benzoyl-n-propylgroup.

As the heterocyclicoxy group of the C₁₋₈ alkyl group substituted with anunsubstituted or substituted heterocyclicoxy group for Q¹, for example,those in which an oxygen atom is bonded to the bonding position of thoseof the heterocyclic group for R can be exemplified. The substituent ofthe heterocycle is not particularly limited and, for example, the samesubstituents as those of the aryl group for X can be exemplified in achemically acceptable range. Specific examples of the C₁₋₈ alkyl groupsubstituted with an unsubstituted or substituted heterocyclicoxy groupinclude a 2-pyridyloxymethyl group, a 2-(2-pyridyloxy)ethyl group, a1-(2-pyridyloxy)ethyl group, a (1-(2-pyridyloxy)-1-methyl)ethyl group, a3-pyridyloxymethyl group, a 2-oxazolyloxymethyl group, and a4-piperazyloxymethyl group.

Among these, Q¹ is preferably an alkenyloxy group in which carbonattached to the oxygen atom is tertiary carbon, such as a1,1-dimethyl-2-propenyloxy group, an alkynyloxy group in which carbonattached to the oxygen atom is tertiary carbon, such as a1,1-dimethyl-2-butynyloxy group, a C₁₋₈ alkoxy group substituted with analkoxycarbonylamino group, a C₁₋₈ alkoxy group substituted with a C₃₋₈cycloalkyl group, a C₁₋₈ branched alkoxy group substituted with anunsubstituted aryl group, a C₁₋₈ alkoxy group substituted with asubstituted aryl group, a C₁₋₈ alkoxy group substituted with asubstituted or unsubstituted heterocyclic group, a C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted C₁₋₈ alkoxy group, aC₁₋₈ alkoxy group substituted with an unsubstituted or substitutedaryloxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted orsubstituted aralkyloxy group, a C₂₋₈ alkynyloxy group substituted withan unsubstituted or substituted aryl group, a C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted C₁₋₈ alkylthio group, aC₁₋₈ alkoxy group substituted with a substituted or unsubstitutedarylthio group, a C₁₋₈ alkoxy group substituted with an unsubstituted orsubstituted C₁₋₈ alkylsulfinyl group, a C₁₋₈ alkoxy group substitutedwith an unsubstituted or substituted arylsulfinyl group, a C₁₋₈ alkoxygroup substituted with an unsubstituted or substituted C₁₋₈alkylsulfonyl group, a C₁₋₈ alkoxy group substituted with anunsubstituted or substituted arylsulfonyl group, a C₁₋₈ alkoxy groupsubstituted with an amino group which is unsubstituted or substitutedwith an (unsubstituted or substituted alkyl group), a C₁₋₈ alkoxy groupwhich is substituted with an amino group substituted with an(unsubstituted or substituted aralkyl group), an unsubstituted orsubstituted aryloxy group, a C₁₋₈ alkyl group substituted with acarboxyl group, a C₁₋₈ alkyl group substituted with an amino group whichis unsubstituted or substituted with an (unsubstituted or substitutedaralkyl group), a C₁₋₈ alkyl group which is substituted with an aminogroup substituted with an (unsubstituted or substituted alkyl group), aC₁₋₈ alkyl group substituted with an unsubstituted or substitutedaryloxy group, an alkyl group substituted with an acyl group, or analkyl group substituted with an unsubstituted or substitutedheterocyclicoxy group, and more preferably an alkenyloxy group in whichcarbon attached to the oxygen atom is tertiary carbon, such as a1,1-dimethyl-2-propenyloxy group, an alkynyloxy group in which carbonattached to the oxygen atom is tertiary carbon, such as a1,1-dimethyl-2-butynyloxy group, a C₁₋₈ alkoxy group substituted with aC₃₋₈ cycloalkyl group, a C₁₋₈ branched alkoxy group substituted with anunsubstituted aryl group, a C₁₋₈ alkoxy group substituted with asubstituted aryl group, a C₁₋₈ alkoxy group substituted with anunsubstituted or substituted heterocyclic group, a C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted C₁₋₈ alkoxy group, aC₁₋₈ alkoxy group substituted with an unsubstituted or substitutedaryloxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted orsubstituted aralkyloxy group, a C₂₋₈ alkynyloxy group substituted withan unsubstituted or substituted aryl group, a C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted C₁₋₈ alkylthio group, aC₁₋₈ alkoxy group substituted with an amino group which is unsubstitutedor substituted with an (unsubstituted or substituted alkyl group), aC₁₋₈ alkoxy group which is substituted with an amino group substitutedwith an (unsubstituted or substituted aralkyl group), a C₁₋₈ alkyl groupsubstituted with an amino group which is unsubstituted or substitutedwith an (unsubstituted or substituted aralkyl group), a C₁₋₈ alkyl groupwhich is substituted with an amino group substituted with an(unsubstituted or substituted alkyl group), a C₁₋₈ alkyl groupsubstituted with an unsubstituted or substituted aryloxy group, a C₁₋₈alkyl group substituted with an acyl group, or a C₁₋₈ alkyl groupsubstituted with an unsubstituted or substituted heterocyclicoxy group.

Furthermore, the alkenyloxy group in which carbon attached to the oxygenatom is tertiary carbon, such as a 1,1-dimethyl-2-propenyloxy group ispreferably a 1,1-dialkyl-substituted alkenyl group, the alkynyloxy groupin which carbon attached to the oxygen atom is tertiary carbon, such asa 1,1-dimethyl-2-butynyloxy group is preferably a1,1-dialkyl-substituted alkynyloxy group, the C₁₋₈ alkoxy groupsubstituted with a C₃₋₈ cycloalkyl is preferably a C₃₋₆ cycloalkyl C₁₋₂alkyl group, the C₁₋₈ branched alkoxy group substituted with anunsubstituted aryl group is preferably a C₁₋₄ branched alkoxy groupsubstituted with an unsubstituted aryl group at the 1- or 2-position,the C₁₋₈ alkoxy group substituted with a substituted aryl group ispreferably a C₁₋₄ alkoxy group which is substituted with an aryl groupsubstituted with a cyano group, a halogen atom, an alkoxy group, analkyl group, an aryl group, or an alkylsulfonyl group, more preferably aC₁₋₄ alkoxy group which is substituted with a substituted aryl groupsubstituted at the 2- or 3-position of the aryl group, and still morepreferably a C₁₋₄ alkyl group which is substituted with an aryl groupsubstituted with a cyano group, a halogen atom, an alkoxy group, analkyl group, an aryl group, or an alkylsulfonyl group at the 2- or3-position, the C₁₋₈ alkoxy group substituted with an unsubstituted orsubstituted heterocyclic group is preferably a C₁₋₄ alkoxy groupsubstituted with an unsubstituted or substituted aromatic heterocyclicgroup, a C₁₋₈ alkoxy group substituted with an unsubstituted orsubstituted C₁₋₈ alkoxy group is preferably a C₁₋₄ alkoxy groupsubstituted with an unsubstituted or substituted C₁₋₄ alkoxy group, theC₁₋₈ alkoxy group substituted with an unsubstituted or substitutedaryloxy group is preferably a C₁₋₄ alkoxy group substituted with anunsubstituted or substituted phenoxy group, the C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted aralkyloxy group ispreferably a C₁₋₄ alkoxy group substituted with an unsubstituted orsubstituted benzyloxy group, the C₂₋₈ alkynyloxy group substituted withan unsubstituted or substituted aryl group is preferably a1,1-dialkyl-substituted C₂₋₈ alkynyloxy group substituted with anunsubstituted or substituted phenyl group, the C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted C₁₋₈ alkylthio group ispreferably a C₁₋₄ alkoxy group substituted with an unsubstituted orsubstituted C₁₋₄ alkylthio group, the C₁₋₈ alkoxy group substituted withan amino group which is unsubstituted or substituted with an(unsubstituted or substituted alkyl group) is preferably a C₁₋₄ alkoxygroup substituted with an amino group which is unsubstituted orsubstituted with an (unsubstituted or substituted alkyl group), the C₁₋₈alkoxy group which is substituted with an amino group substituted withan (unsubstituted or substituted aralkyl group) is preferably C₁₋₄alkoxy group which is substituted with an amino group substituted withan (unsubstituted or substituted (benzyl group or phenethyl group)), theC₁₋₈ alkyl group substituted with an amino group which is unsubstitutedor substituted with an (unsubstituted or substituted aralkyl group) ispreferably a C₁₋₄ alkyl group substituted with an amino group which isunsubstituted or substituted with an (unsubstituted or substituted(benzyl group or phenethyl group)), the C₁₋₈ alkyl group which issubstituted with an amino group substituted with an (unsubstituted orsubstituted alkyl group) is preferably a C₁₋₄ alkyl group which issubstituted with an amino group substituted with an (unsubstituted orsubstituted alkyl group), the C₁₋₈ alkyl group substituted with anunsubstituted or substituted aryloxy group is preferably a C₁₋₄ alkylgroup substituted with an unsubstituted or substituted phenoxy group,the C₁₋₈ alkyl group substituted with an acyl group is preferably a C₁₋₄alkyl group substituted with a formyl group or an alkylcarbonyl group,or the C₁₋₈ alkyl group substituted with an unsubstituted or substitutedheterocyclicoxy group is preferably a C₁₋₄ alkyl group substituted withan unsubstituted or substituted aromatic heterocyclicoxy group.

When n2 is 1 and R is a halogen atom, Z represents a hydrogen atom, anamino group, or a group represented by formula: Q²C(═O)NH— (in which Q²represents a hydrogen atom, a C₁₋₈ haloalkyl group, a C₂₋₈ alkenylgroup, a C₂₋₈ haloalkenyl group, a C₂₋₈ alkynyl group, a C₂₋₈haloalkynyl group, a C₁₋₈ alkoxy group, a C₁₋₈ haloalkoxy group, a C₂₋₈alkenyloxy group, a C₂₋₈ haloalkenyloxy group, a C₂₋₈ alkynyloxy group,a C₂₋₈ haloalkynyloxy group, a C₃₋₈ cycloalkyl group, a C₃₋₈cycloalkyloxy group, a C₁₋₈ alkylamino group, a C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted amino group, a C₁₋₈alkoxy group substituted with a C₃₋₈ cycloalkyl group, an unsubstitutedor substituted aralkyloxy group, a C₁₋₈ alkoxy group substituted with asubstituted or unsubstituted heterocyclic group, a C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted C₁₋₈ alkoxy group, aC₁₋₈ alkoxy group substituted with an unsubstituted or substitutedaryloxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted orsubstituted aralkyloxy group, a C₂₋₈ alkynyloxy group substituted withan unsubstituted or substituted aryl group, a C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted C₁₋₈ alkylthio group, aC₁₋₈ alkoxy group substituted with a substituted or unsubstitutedarylthio group, a C₁₋₈ alkoxy group substituted with an unsubstituted orsubstituted C₁₋₈ alkylsulfinyl group, a C₁₋₈ alkoxy group substitutedwith an unsubstituted or substituted arylsulfinyl group, a C₁₋₈ alkoxygroup substituted with an unsubstituted or substituted C₁₋₈alkylsulfonyl group, a C₁₋₈ alkoxy group substituted with anunsubstituted or substituted arylsulfonyl group, an unsubstituted orsubstituted aryloxy group, a C₁₋₈ alkyl group substituted with acarboxyl group, a C₁₋₈ alkyl group substituted with an unsubstituted orsubstituted amino group, a C₁₋₈ alkyl group substituted with anunsubstituted or substituted aryloxy group, a C₁₋₈ alkyl groupsubstituted with an unsubstituted or substituted C₁₋₈ alkylthio group, aC₁₋₈ alkyl group substituted with an unsubstituted or substituted alkoxygroup, a C₁₋₈ alkyl group substituted with an acyl group, or a C₁₋₈alkyl group substituted with an unsubstituted or substitutedheterocyclicoxy group).

Specific examples of the C₁₋₈ haloalkyl group, the C₂₋₈ haloalkenylgroup, the C₂₋₈ alkynyl group, the C₂₋₈ haloalkynyl group, the C₁₋₈haloalkoxy group, the C₂₋₈ alkenyloxy group, the C₂₋₈ haloalkenyloxygroup, the C₂₋₈ alkynyloxy group, the C₂₋₈ haloalkynyloxy group, theC₁₋₈ alkoxy group substituted with an C₃₋₈ cycloalkyl group, the C₁₋₈alkoxy group substituted with a substituted or unsubstitutedheterocyclic group, the C₁₋₈ alkoxy group substituted with anunsubstituted or substituted C₁₋₈ alkoxy group, the C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted aryloxy group, the C₁₋₈alkoxy group substituted with an unsubstituted or substituted aralkyloxygroup, the C₂₋₈ alkynyloxy group substituted with an unsubstituted orsubstituted aryl group, the C₁₋₈ alkoxy group substituted with anunsubstituted or substituted C₁₋₈ alkylthio group, the C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted arylthio group, theC₁₋₈ alkoxy group substituted with an unsubstituted or substitutedC₁₋₈alkylsulfinyl group, the C₁₋₈ alkoxy group substituted with anunsubstituted or substituted arylsulfinyl group, the C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted C₁₋₈ alkylsulfonylgroup, the C₁₋₈ alkoxy group substituted with an unsubstituted orsubstituted arylsulfonyl group, the unsubstituted or substituted aryloxygroup, the C₁₋₈ alkyl group substituted with a carboxyl group, the C₁₋₈alkyl group substituted with an unsubstituted or substituted aryloxygroup, the C₁₋₈ alkyl group substituted with an acyl group, the or C₁₋₈alkyl group substituted with an unsubstituted or substitutedheterocyclicoxy group for Q² include the same specific examples as thoseof Q¹.

Specific examples of the C₃₋₈ cycloalkyl group for Q² include acyclopropyl group, a cyclohexyl group, a cyclobutyl group, a cyclopentylgroup, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

Specific examples of the C₃₋₈ cycloalkyloxy group for Q² include acyclopropyloxy group, a cyclohexyloxy group, a cyclobutyloxy group, acyclopentyloxy group, a cyclohexyloxy group, a cycloheptyloxy group, anda cyclooctyloxy group.

Specific examples of the C₁₋₈ alkylamino group for Q² include amethylamino group, a diethylamino group, an ethylmethylamino group, a din-heptylamino group, and a t-butylamino group.

The substituent of the amino group of the C₁₋₈ alkoxy group substitutedwith an unsubstituted or substituted amino group for Q² is notparticularly limited and, for example, the same substituents as those ofthe aryl group for X can be exemplified in a chemically acceptablerange. Specific examples of the C₁₋₈ alkoxy group substituted with anunsubstituted or substituted amino group include a 2-aminoethoxy group,a 6-aminohexyloxy group, an N-acetylaminomethoxy group, a2-(N-acetylamino)ethoxy group, a 1-(N-acetylamino)ethoxy group, a2-(N-acetyl-N-methylamino)ethoxy group, a 2-(N-benzoyl)aminoethoxygroup, an N-methoxycarbonylaminomethoxy group, anN-t-butoxycarbonylaminomethoxy group, a 2-(N-ethoxycarbonylamino)ethoxygroup, and a 2-(N-t-butoxycarbonyl-N-benzylamino) ethoxy group.

Specific examples of the aralkyloxy group of the unsubstituted orsubstituted aralkyloxy group for Q² include a benzyloxy group, aphenethyloxy group, and a 1-naphthylmethoxy group. The substituentthereof is not particularly limited and, for example, the samesubstituents as those of the aryl group for X can be exemplified in achemically acceptable range. Specific examples of the unsubstituted orsubstituted aralkyloxy group include a benzyloxy group, a phenethyloxygroup, a 1-phenylethoxy group, a 1-phenyl-1-methylethoxy group, a2-phenyl-1-methylethoxy group, a 2-methylphenylmethoxy group, a3-methylphenylmethoxy group, a 4-chlorophenylmethoxy group, a1-(4-chlorophenyl)ethoxy group, a 3-chlorophenylmethoxy group, a2-methoxyphenylmethoxy group, a 3-methoxyphenylmethoxy group, a4-methylsulfonylphenylmethoxy group, and a 3-phenylphenylmethoxy group.

Specific examples of the alkylthio group of the C₁₋₈ alkyl groupsubstituted with an unsubstituted or substituted C₁₋₈ alkylthio groupfor Q² include a methylthio group, an ethylthio group, an n-propylthiogroup, an isopropylthio group, an n-butylthio group, an isobutylthiogroup, an s-butylthio group, and a t-butylthio group. The substituent isnot particularly limited and, for example, the same substituents asthose of the aryl group for X can be exemplified in a chemicallyacceptable range. Specific examples of the C₁₋₈ alkyl group substitutedwith an unsubstituted or substituted C₁₋₈ alkylthio group include amethylthiomethyl group, a methylthio-n-butyl group, and a1-methylthioethyl group.

As the alkoxy group of the C₁₋₈ alkyl group substituted with anunsubstituted or substituted alkoxy group for Q², for example, the samealkoxy groups as those for X can be exemplified. The substituent thereofis not particularly limited and, for example, the same substituents asthose of the aryl group for X can be exemplified in a chemicallyacceptable range. Specific examples of the C₁₋₈ alkyl group substitutedwith an unsubstituted or substituted alkoxy group include amethoxymethyl group, an ethoxymethyl group, a 2-isopropoxyethyl group,an n-propoxyethyl group, a t-butoxy-1-butyl group, a2-(2-methoxyethoxy)ethyl group, a 2-trifluoromethoxyethyl group, and a2-pentafluoroethoxyethyl group.

Among these, Z is preferably a group represented by formula: Q²C(═O)NH—,and Q² is preferably a C₂₋₈ haloalkenyl group, a C₂₋₈ alkynyl group, aC₂₋₈ haloalkynyl group, a C₁₋₈ haloalkoxy group, a C₂₋₈ alkenyloxygroup, a C₂₋₈ haloalkenyloxy group, a C₂₋₈ alkynyloxy group, a C₂₋₈haloalkynyloxy group, a C₁₋₈ alkoxy group substituted with an aminogroup which is unsubstituted or substituted with an (unsubstituted orsubstituted alkyl group), a C₁₋₈ alkoxy group which is substituted withan amino group substituted with an (unsubstituted or substituted aralkylgroup), a C₁₋₈ alkoxy group substituted with an alkoxycarbonylaminogroup, a C₁₋₈ alkoxy group substituted with a C₃₋₈ cycloalkyl group, aC₁₋₈ branched alkoxy group substituted with an unsubstituted aryl group,a C₁₋₈ alkoxy group substituted with a substituted aryl group, a C₁₋₈alkoxy group substituted with a substituted or unsubstitutedheterocyclic group, a C₁₋₈ alkoxy group substituted with anunsubstituted or substituted C₁₋₈ alkoxy group, a C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted aryloxy group, a C₁₋₈alkoxy group substituted with an unsubstituted or substituted aralkyloxygroup, a C₂₋₈ alkynyloxy group substituted with an unsubstituted orsubstituted aryl group, a C₁₋₈ alkoxy group substituted with anunsubstituted or substituted C₁₋₈ alkylthio group, a C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted arylthio group, a C₁₋₈alkoxy group substituted with an unsubstituted or substituted C₁₋₈alkylsulfinyl group, a C₁₋₈ alkoxy group substituted with anunsubstituted or substituted arylsulfinyl group, a C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted C₁₋₈ alkylsulfonylgroup, a C₁₋₈ alkoxy group substituted with an unsubstituted orsubstituted arylsulfonyl group, an unsubstituted or substituted aryloxygroup, a C₁₋₈ alkyl group substituted with a carboxyl group, a C₁₋₈alkyl group which is substituted with an amino group substituted with an(unsubstituted or substituted alkyl group), a C₁₋₈ alkyl groupsubstituted with an amino group which is unsubstituted or substitutedwith an (unsubstituted or substituted aralkyl group), a C₁₋₈ alkyl groupsubstituted with an unsubstituted or substituted aryloxy group, a C₁₋₈alkyl group substituted with an amino group, or a C₁₋₈ alkyl groupsubstituted with an unsubstituted or substituted heterocyclicoxy group,and more preferably an alkenyloxy group, in which carbon attached to theoxygen atom is tertiary carbon, such as a 1,1-dimethyl-2-propenyloxygroup, an alkynyloxy group in which carbon attached to the oxygen atomis tertiary carbon, such as a 1,1-dimethyl-2-butynyloxy group, a C₁₋₈alkoxy group substituted with a C₃₋₈ cycloalkyl group, a C₁₋₈ branchedalkoxy group substituted with an unsubstituted aryl group, a C₁₋₈ alkoxygroup substituted with a substituted aryl group, a C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted heterocyclic group, aC₁₋₈ alkoxy group substituted with an unsubstituted or substituted C₁₋₈alkoxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted orsubstituted aryloxy group, a C₁₋₈ alkoxy group substituted with anunsubstituted or substituted aralkyloxy group, a C₂₋₈ alkynyloxy groupsubstituted with an unsubstituted or substituted aryl group, a C₁₋₈alkoxy group substituted with an unsubstituted or substituted C₁₋₈alkylthio group, a C₁₋₈ alkoxy group substituted with an amino groupwhich is unsubstituted or substituted with an (unsubstituted orsubstituted alkyl group), a C₁₋₈ alkoxy group which is substituted withan amino group substituted with an (unsubstituted or substituted aralkylgroup), a C₁₋₈ alkyl group substituted with an amino group which isunsubstituted or substituted with an (unsubstituted or substitutedaralkyl group), a C₁₋₈ alkyl group which is substituted with an aminogroup substituted with an (unsubstituted or substituted alkyl group), aC₁₋₈ alkyl group substituted with an unsubstituted or substitutedaryloxy group, a C₁₋₈ alkyl group substituted with an acyl group, or aC₁₋₈ alkyl group substituted with an unsubstituted or substitutedheterocyclicoxy group.

As more preferred above functional groups, the same as those for Q¹ canbe exemplified.

When n2 is 1 or more and at least one R is a cyano group, a nitro group,a hydroxyl group, a thiol group, a formyl group, a carboxyl group, anunsubstituted or substituted amino group, an unsubstituted orsubstituted C₁₋₈ alkyl group, an unsubstituted or substituted C₂₋₈alkenyl group, an unsubstituted or substituted C₂₋₈ alkynyl group, anunsubstituted or substituted aryl group, an unsubstituted or substitutedheterocyclic group, OR¹, S(O)_(m)R¹, COR¹, or CO₂R¹, or n2 is 2 or moreand at least two R(s) are halogen atoms, Z represents a hydrogen atom,an amino group, or a group represented by formula: Q³C(═O)NH-(in whichQ³ represents a hydrogen atom, a C₁₋₈ alkyl group, a C₁₋₈ haloalkylgroup, a C₂₋₈ alkenyl group, a C₂₋₈ haloalkenyl group, a C₂₋₈ alkynylgroup, a C₂₋₈ haloalkynyl group, a C₁₋₈ alkoxy group, a C₁₋₈ haloalkoxygroup, a C₂₋₈ alkenyloxy group, a C₂₋₈ haloalkenyloxy group, a C₂₋₈alkynyloxy group, a C₂₋₈ haloalkynyloxy group, a C₃₋₈ cycloalkyl group,a C₃₋₈ cycloalkyloxy group, a C₁₋₈ alkylamino group, a C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted amino group, a C₁₋₈alkoxy group substituted with a C₃₋₈ cycloalkyl group, an unsubstitutedor substituted aralkyloxy group, a C₁₋₈ alkoxy group substituted with anunsubstituted or substituted heterocyclic group, a C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted C₁₋₈ alkoxy group, aC₁₋₈ alkoxy group substituted with an unsubstituted or substitutedaryloxy group, a C₁₋₈ alkoxy group substituted with an unsubstituted orsubstituted aralkyloxy group, a C₂₋₈ alkynyloxy group substituted withan unsubstituted or substituted aryl group, a C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted C₁₋₈ alkylthio group, aC₁₋₈ alkoxy group substituted with a substituted or unsubstitutedarylthio group, a C₁₋₈ alkoxy group substituted with an unsubstituted orsubstituted C₁₋₈ alkylsulfinyl group, a C₁₋₈ alkoxy group substitutedwith an unsubstituted or substituted arylsulfinyl group, C₁₋₈ alkoxygroup substituted with an unsubstituted or substituted C₁₋₈alkylsulfonyl group, a C₁₋₈ alkoxy group substituted with anunsubstituted or substituted arylsulfonyl group, an unsubstituted orsubstituted aryloxy group, a C₁₋₈ alkyl group substituted with acarboxyl group, a C₁₋₈ alkyl group substituted with an unsubstituted orsubstituted amino group, a C₁₋₈ alkyl group substituted with anunsubstituted or substituted aryloxy group, a C₁₋₈ alkyl groupsubstituted with an unsubstituted or substituted C₁₋₈ alkylthio group, aC₁₋₈ alkyl group substituted with an unsubstituted or substituted alkoxygroup, a C₁₋₈ alkyl group substituted with an acyl group, or a C₁₋₈alkyl group substituted with an unsubstituted or substitutedheterocyclicoxy group).

As the C₁₋₈ alkyl group for Q³, for example, the same as those of C₁₋₈alkyl group for X can be exemplified.

As specific examples of other functional group contained in Q³, the sameas those for Q² can be exemplified.

Among these, formula: Q³C(═O)NH— is preferable. Among these, Q³ ispreferably a C₁₋₈ alkyl group, a C₁₋₈ haloalkyl group, a C₂₋₈ alkenylgroup, a C₁₋₈ alkoxy group, a C₂₋₈ alkenyloxy group, a C₂₋₈ alkynyloxygroup, a C₃₋₈ cycloalkyl group, a C₃₋₈ cycloalkyloxy group, a C₁₋₈alkylamino group, a C₁₋₈ alkoxy group substituted with an unsubstitutedor substituted amino group, a C₁₋₈ alkoxy group substituted with a C₃₋₈cycloalkyl group, an unsubstituted or substituted aralkyloxy group, aC₁₋₈ alkoxy group substituted with an unsubstituted or substitutedheterocyclic group, a C₁₋₈ alkoxy group substituted with anunsubstituted or substituted C₁₋₈ alkoxy group, a C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted aryloxy group, a C₁₋₈alkoxy group substituted with an unsubstituted or substituted aralkyloxygroup, a C₂₋₈ alkynyloxy group substituted with an unsubstituted orsubstituted aryl group, a C₁₋₈ alkoxy group substituted with anunsubstituted or substituted C₁₋₈ alkylthio group, a C₁₋₈ alkoxy groupsubstituted with an unsubstituted or substituted arylthio group, a C₁₋₈alkoxy group substituted with an unsubstituted or substituted C₁₋₈alkylsulfinyl group, C₁₋₈ alkoxy group substituted with an unsubstitutedor substituted arylsulfinyl group, a C₁₋₈ alkoxy group substituted withan unsubstituted or substituted C₁₋₈ alkylsulfonyl group, a C₁₋₈ alkoxygroup substituted with an unsubstituted or substituted arylsulfonylgroup, an unsubstituted or substituted aryloxy group, a C₁₋₈ alkyl groupsubstituted with a carboxyl group, a C₁₋₈ alkyl group substituted withan unsubstituted or substituted amino group, a C₁₋₈ alkyl groupsubstituted with an unsubstituted or substituted aryloxy group, a C₁₋₈alkyl group substituted with an unsubstituted or substituted C₁₋₈alkylthio group, a C₁₋₈ alkyl group substituted with an unsubstituted orsubstituted alkoxy group, a C₁₋₈ alkyl group substituted with an acylgroup, or a C₁₋₈ alkyl group substituted with an unsubstituted orsubstituted heterocyclicoxy group, and still more prefereably the sameas those for Q¹.

In formula (5), R¹¹ represents a hydrogen atom, a halogen atom, a cyanogroup, a nitro group, a hydroxyl group, a thiol group, an unsubstitutedor substituted amino group, an unsubstituted or substituted C₁₋₈ alkylgroup, an unsubstituted or substituted C₂₋₈ alkenyl group, anunsubstituted or substituted C₂₋₈ alkynyl group, an unsubstituted orsubstituted aryl group, an unsubstituted or substituted heterocyclicgroup, OR¹, S(O)_(m)R¹, COR¹, or CO₂R¹.

R¹ is the same as defined above.

When R¹¹ is a hydrogen atom, Z¹¹ represents a group represented byformula: Q¹C(═O)NH— (in which Q¹ is the same as defined above).

When R¹¹ is a halogen atom, Z¹¹ represents a hydrogen atom, an aminogroup, or a group represented by formula: Q²C(═O)NH— (in which Q² is thesame as defined above).

When R¹¹ is a cyano group, a nitro group, a hydroxyl group, a thiolgroup, an unsubstituted or substituted amino group, an unsubstituted orsubstituted C₁₋₈ alkyl group, an unsubstituted or substituted C₂₋₈alkenyl group, an unsubstituted or substituted C₂₋₈ alkynyl group, anunsubstituted or substituted aryl group, an unsubstituted or substitutedheterocyclic group, OR¹, S(O)_(m)R¹, COR¹, or CO₂R¹, Z¹¹ represents ahydrogen atom, an amino group, or a group represented by formula:Q³C(═O)NH— (in which Q³ is the same as defined above).

As the specific examples of R¹¹, the same specific examples as those forR in formula (4) can be exemplified. As the specific examples of Z¹¹,the same specific examples as those for Z in formula (4) can beexemplified.

As preferred Z¹¹, the same as those for Z can be exemplified.

Stereoisomers of (E) and (Z) isomers, based on the double bond ofcarbon-nitrogen in the oxime moiety, exist in the tetrazoyloximederivative represented by formula (1). These two stereoisomers and amixture thereof are included in the present invention. The synthesizedproduct is usually obtained in the form of the (Z) isomer only, or amixture of (E) and (Z) isomers. Each of (E) and (Z) isomers can beisolated by separation and purification, known methods such as silicagel chromatography. Both (Z) and (E) isomers have activity and (Z)isomer is particularly preferable.

Salts of the compound represented by formula (1) are not particularlylimited as long as they are agriculturally or horiculturally acceptablesalts. Examples of the salts include salts of inorganic acids, such ashydrochloride, nitrate, sulfate, and phosphate; and salts of organicacids, such as acetate, lactate, propionate, and benzoate.

(Preparation Method)

The tetrazoyloxime derivative represented by formula (1) can beprepared, for example, by the method described in pamphlet of WO03/016303.

(In the above formulas, A, X, Het and n1 is the same as defined above,and L represents a leaving group such as halogen atom.)

That is to say, the compound represented by formula (1) of the presentinvention can be obtained by reacting an oxime compound represented byformula (6) with a compound represented by formula (7) in the presenceof a base.

As the base used for the reaction, inorganic bases such as sodiumhydroxide, potassium hydroxide, sodium hydride, sodium carbonate, andpotassium carbonate; and organic bases such as triethylamine,4-(dimethylamino)pyridine, and pyridine can be used. These bases can beused alone, or two or more kinds of them can be used in combination.

The used amount of the base is usually from 0.01 to 100 mol, andpreferably from 0.1 to 5 mol, per mol of the compopund represented byformula (6).

This reaction can be performed in the presence or absence of a solvent.

The solvent to be used is not particularly limited as long as it is asolvent which is inert to the present reaction. Examples of the solventinclude hydrocarbon-based solvents such as pentane, hexane, heptane,benzene, toluene, and xylene; halogen-based solvents such asdichloromethane, chloroform, and hydrocarbon tetrachloride;nitrile-based solvents such as acetonitrile and propionitrile;ether-based solvents such as diethylether, dioxane, and tetrahydrofuran;amide-based solvents such as N,N-dimethylformamide,N,N-dimethylacetamide, and N-methyl pyrrolidone; sulfoxide-basedsolvents such as dimethyl sulfoxide; water; and a mixed solvent thereof.

The reaction temperature of the reaction is usually within a range from−70° C. to +200° C., and preferably from −20° C. to +100° C.

The reaction time varies depending on the reaction scale, but is usuallywithin a range from 30 minutes to 24 hours.

Salts of the compound represented by formula (1) can be prepared byreacting the compound represented by formula (1) with an acid by aconventional method.

After completion of any reaction, the objective compound represented byformula (1) and a salt thereof can be isolated by performing a usualwork-up operation. If it is necessary to purify the product,conventionally known purification means such as distillation,recrystallization or column chromatography can be employed.

Specific examples of the thus prepared tetrazoyloxime derivativerepresented by formula (1) of the present invention are shown in Table 1to Table 4 shown below. Abbreviations in the tables have meanings shownbelow. Me: methyl, Et: ethyl, Pr: propyl, Bu: butyl, Hex: hexyl, i: iso,n: normal, s: secondary, t: tertiary, c: cyclo, Ph: phenyl, and Py:pyridyl

TABLE 1

mp No Z R_(n2) (X)_(n1) ° C. 1-1 H 4-Me — 1-2 NH₂ 4-Me — 1-3 NH₂ 4-Bu-t— 1-4 NH₂ 4-OC₂H₅ — 1-5 NH₂ 5-CH₃ — 1-6 NH₂ 4-OCH₃ — 1-7 NH₂ 4-C₂H₅ —1-8 NHCHO 4-Me — 1-9 NHCOCH₃ 4-Me — 1-10 NHCOC₂H₅ 4-Me — 1-11 NHCOPr-n4-Me — 1-12 NHCOPr-i 4-Me — 1-13 NHCOBu-n 4-Me — 1-14 NHCOBu-i 4-Me —1-15 NHCOBu-s 4-Me — 1-16 NHCOBu-t 4-Me — 1-17 NHCOBu-t 4-OMe — 1-18NHCOCH₂CF₃ 4-Me — 1-19 NHCOC₂H₅ 4-Me — 1-20 NHCOCH₂CH₂F 4-Me — 1-21NHCOC(CH₃)₂CF₃ 4-Me — 1-22 NHCOCH₂CH₂CF₃ 4-Me — 1-23 NHCOCH₂C₂F₅ 4-Me —1-24 NHCOCH₂CH═CH₂ 4-Me — 1-25 NHCOCH₂CH═CMe₂ 4-Me — 1-26NHCOC(CH₃)₂CH═CH₂ 4-Me — 1-27 NHCOC(CH₃)₂CH═CHCH₃ 4-Me — 1-28NHCOCH₂CH═CHCl 4-Me — 1-29 NHCOCH₂CH═CHCF₃ 4-Me — 1-30 NHCOCH₂CI═CI₂4-Me — 1-31 NHCO(1,1-dimethyl-2- 4-Me — propynyl) 1-32 NHCO(2-butynyl)4-Me — 1-33 NHCO(1,1-dimethyl-2- 4-Me — butynyl) 1-34NHCO(1,1-dimethyl-2- 4-Me — pentynyl) 1-35 NHCO(1-propynyl) 4-Me — 1-36NHCO(1,1-dimethyl-3-Iodo- 4-Me — 2-pentnyl) 1-37 NHCO(4,4,4-trifluoro-2-4-Me — butynyl) 1-38 NHCOPr-c 4-Me — 1-39 NHCOHex-c 4-Me — 1-40NHCO(CH₂)₄CO₂H 4-Me — 1-41 NHCOCH₂CH₂NHCOBu-t 4-Me — 1-42NHCOCH₂CH₂NHCO₂Et 4-Me — 1-43 NHCOCH₂CH₂CH₂NHCOCH₃ 4-Me — 1-44NHCOCH₂CH₂CH₂NHMe 4-Me — 1-45 NHCOCH₂CH₂N(Me)COCH₃ 4-Me — 1-46NHCOCH₂CH₂NHCOPh 4-Me — 1-47 NHCOCH₂CH₂N(Me)COPh 4-Me — 1-48NHCOCH₂CH₂NHPh 4-Me — 1-49 NHCO(CH₂)₄NH₂ 4-Me — 1-50 NHCOCH₂NHCH₂Ph 4-Me— 1-51 NHCOCH₂N(CH₂Ph)(CO₂Bu-t) 4-Me — 1-52 NHCOCH₂CH₂OC₆H₄Cl-4 4-Me —1-53 NHCOCH₂OPh 4-Me — 1-54 NHCOCH₂OC₆H₄F-3 4-Me — 1-55NHCOCH₂OC₆H₄OCF₃-3 4-Me — 1-56 NHCO(CH₂)₄SMe 4-Me — 1-57 NHCOCH₂CH₂OEt4-Me — 1-58 NHCOCH₂CH₂OPr-i 4-Me — 1-59 NHCOCH₂CH₂OBu-i 4-Me — 1-60NHCOCH₂CH₂OCH₂CH₂OMe 4-Me — 1-61 NHCO₂CH₃ 4-Me — 1-62 NHCO₂C₂H₅ 4-Me —1-63 NHCO₂Pr-n 4-Me — 1-64 NHCO₂Pr-i 4-Me — 1-65 NHCO₂Bu-i 4-Me — 1-66NHCO₂Bu-n 4-Me — 1-67 NHCO₂Bu-s 4-Me — 1-68 NHCO₂Bu-t 4-i-Pr — 68-701-69 NHCO₂Bu-t 5-Me — 60-63 1-70 NHCO₂Bu-t 4-t-Bu — 68-69 1-71 NHCO₂Bu-t4-Me — 1-72 NHCO₂Bu-t 4-Et — 42-46 1-73 NHCO₂Bu-t 4-CH═CH2 — 1-74NHCO₂Bu-t 4-OMe — 151- 153 1-75 NHCO₂Bu-t 4-OEt — 54-55 1-76 NHCO₂Bu-t4-OCH₂CH₂OEt — <50 1-77 NHCO₂Bu-t 4-OPr-i — 1-78 NHCO₂Bu-t 4-OBu-n —1-79 NHCO₂Bu-t 4-SMe — 142- 144 1-80 NHCO₂Bu-t 4-SOMe — 86-88 1-81NHCO₂Bu-t 4-SO₂Me — 117- 118 1-82 NHCO₂Bu-t 4-NMe₂ — 1-83 NHCO₂Bu-t4-N(Me) — (CO₂Bu-t) 1-84 NHCO₂Bu-t 5-CN — 68-72 1-85 NHCO₂Bu-t 4-CN —70-75 1-86 NHCO₂Bu-t 4-morpholino — 1-87 NHCO₂Bu-t 5-Ph — 99- 102 1-88NHCO₂Bu-t 5-CO₂C₂H₅ — 74-77 1-89 NHCO₂Bu-t 5-CONHCH₃ — 1-90 NHCO₂Bu-tCF₃ — 1-91 NHCO₂Bu-t 5-OH — 1-92 NHCO₂Bu-t 5-SH — 1-93 NHCO₂Bu-t4-CH₂CI═CI₂ — 1-94 NHCO₂Bu-t 4-etynyl — 1-95 NHCO₂Bu-t 4-propargyl —1-96 NHCO₂Bu-t 4-(3-iodo-2- — propynyl) 1-97 NHCO₂Bu-t 4-Ph — 1-98NHCO₂Bu-t 4-C₆H₄OMe-4 — 1-99 NHCO₂Bu-t 4-(2-pyridyl) — 1-100 NHCO₂Bu-t4-(4-CH₃-2- — oxazolyl) 1-101 NHCO₂Bu-t 4-(3-CF₃-5- — Cl-2-pyridyl)1-102 NHCO₂Bu-t 4-pyrrolidino — 1-103 NHCO₂Bu-t 4-COMe — 1-104 NHCO₂Bu-t4-CONHMe — 1-105 NHCO₂Bu-t 4-CONMe₂ — 1-106 NHCO₂Bu-t 4-COPr-c — 1-107NHCO₂Bu-t 4-COPh — 1-108 NHCO₂Bu-t 4- — COCH₂CH═CH₂ 1-109 NHCO₂Bu-t4-CO(propargyl) — 1-110 NHCO₂Bu-t 4-CO₂Me — 1-111 NHCO₂Bu-t 4-CO₂Ph —1-112 NHCO₂Bu-t 4- — CO₂CH₂CH═CH₂ 1-113 NHCO₂Bu-t 4-CO₂(propargyl) —1-114 NHCO₂Bu-t 4-Me 2-Cl 1-115 NHCO₂Bu-t 4-Me 3-Cl 1-116 NHCO₂Bu-t 4-Me4-Cl 1-117 NHCO₂Bu-t 4-Me 2,4-Cl₂ 1-118 NHCO₂Bu-t 4-Me 3,5-Cl₂ 1-119NHCO₂Bu-t 4-Me 3,4,5- Cl₃ 1-120 NHCO₂Bu-t 4-Me 2-Me 1-121 NHCO₂Bu-t3,4-diMe — 1-122 NHCO₂Bu-t 3,5-diMe — 1-123 NHCO₂Bu-t 4,5-diMe — 1-124NHCO₂Bu-t 3,4,5-triMe — 1-125 NHCO₂Bu-t 3-Cl-4-Me — 1-126 NHCO₂Bu-t5-Cl-4-Me — 1-127 NHCO₂Bu-t 3,5-diCl-4-Me — 1-128 NHCO₂Bu-t 3,5-diCl —1-129 NHCO₂Bu-t 3,4-diCl — 1-130 NHCO₂Bu-t 3,4-diF — 1-131 NHCO₂Bu-n4-NH₂ — 1-132 NHCO₂Bu-n 4-NHCO₂Bu-t — 1-133 NHCO₂CH₂CF₃ 4-Me — 1-134NHCO₂C₂F₅ 4-Me — 1-135 NHCO₂CH₂CH₂F 4-Me — 1-136 NHCO₂C(CH₃)₂CF₃ 4-Me —1-137 NHCO₂CH₂CH₂CF₃ 4-Me — 1-138 NHCO₂CH₂C₂F₅ 4-Me — 1-139NHCO₂CH₂CH═CH₂ 4-Me — 1-140 NHCO₂CH₂CH═CMe₂ 4-Me — 1-141NHCO₂C(CH₃)₂CH═CH₂ 4-Me — 1-142 NHCO₂C(CH₃)₂CH═CHCH₃ 4-Me — 1-143NHCO₂CH₂CH═CHCl 4-Me — 1-144 NHCO₂CH₂CH═CHCF₃ 4-Me — 1-145NHCO₂CH₂CI═CI₂ 4-Me — 1-146 NHCO₂(1,1-dimethyl-2- 4-Me — propynyl) 1-147NHCO₂(2-butynyl) 4-Me — 1-148 NHCO₂(1,1-dimethyl-2- 4-Me — butynyl)1-149 NHCO₂(1,1-dimethyl-2- 4-Me — pentynyl) 1-150 NHCO₂(1-propynyl)4-Me — 1-151 NHCO₂(1,1-dimethyl-3-Iodo- 4-Me — 2-pentynyl) 1-152NHCO₂(4,4,4-trifluoro-2- 4-Me — butynyl) 1-153 NHCO₂Pr-c 4-Me — 1-154NHCO₂Hex-c 4-Me — 1-155 NHCO₂CH₂CH₂NHCO₂Bu-t 4-Me — 1-156NHCO₂CH₂CH₂NHCO₂Et 4-Me — 1-157 NHCO₂CH₂CH₂CH₂NHCOCH₃ 4-Me — 1-158NHCO₂CH₂CH₂CH₂NHMe₂ 4-Me — 1-159 NHCO₂CH₂CH₂N(Me)COCH₃ 4-Me — 1-160NHCO₂CH₂CH₂NHCOPh 4-Me — 1-161 NHCO₂CH₂CH₂N(Me)COPh 4-Me — 1-162NHCO₂CH₂CH₂NHPh 4-Me — 1-163 NHCO₂(CH₂)₄NH₂ 4-Me — 1-164 NHCO₂CH₂NHCH₂Ph4-Me — 1-165 NHCO₂CH₂N(CH₂Ph)(CO₂Bu-t) 4-Me — 1-166 NHCO₂CH₂C₃H₅-c 4-Me— 1-167 NHCO₂CH(CH₃)C₃H₅-c 4-Me — 1-168 NHCO₂CH₂C₆H₁₁-c 4-Me — 1-169NHCO₂CH₂Ph 4-Me — 1-170 NHCO₂CH(CH₃)CH₂Ph 4-Me — 1-171 NHCO₂CH(CH₃)Ph4-Me — 1-172 NHCO₂C(CH₃)₂Ph 4-Me — 1-173 NHCO₂CH₂C₆H₄CF₃-4 4-Me — 1-174NHCO₂CH₂C₆H₄CN-4 4-Me — 1-175 NHCO₂CH₂C₆H₄CN-3 4-Me — 1-176NHCO₂CH₂C₆H₄Cl-4 4-Me — 1-177 NHCO₂CH₂C₆H₄Cl-3 4-Me — 1-178NHCO₂CH₂C₆H₄OMe-3 4-Me — 1-179 NHCO₂CH₂C₆H₄OMe-2 4-Me — 1-180NHCO₂CH₂C₆H₄Me-4 4-Me — 1-181 NHCO₂CH₂C₆H₄Me-3 4-Me — 1-182NHCO₂CH₂C₆H₄Me-2 4-Me — 1-183 NHCO₂CH₂C₆H₄SO₂Me-4 4-Me — 1-184NHCO₂CH₂C₆H₄SO₂Me-3 4-Me — 1-185 NHCO₂CH₂C₆H₄Ph-4 4-Me — 1-186NHCO₂CH₂C₆H₄Ph-3 4-Me — 1-187 NHCO₂CH₂Py-2 4-Me — 1-188NHCO₂CH₂(6-Me-2-Py) 4-Me — 1-189 NHCO₂C(CH₃)₂Py-4 4-Me — 1-190NHCO₂CH₂(2-thiazolyl) 4-Me — 1-191 NHCO₂CH₂(2-benzthiazolyl) 4-Me —1-192 NHCO₂CH₂CH₂OMe 4-Me — 1-193 NHCO₂CH₂CH₂OEt 4-Me — 1-194NHCO₂CH₂CH₂OPr-i 4-Me — 1-195 NHCO₂CH₂CH₂OBu-i 4-Me — 1-196NHCO₂CH₂CH₂OCH₂CH₂OMe 4-Me — 1-197 NHCO₂CH₂CH₂OEt 4-i-Pr — 1-198NHCO₂CH₂CH₂OC₆H₄Cl-4 4-Me — 1-199 NHCOCH₂OPh 4-Me — 1-200NHCOCH₂OC₆H₄F-3 4-Me — 1-201 NHCOCH₂OC₆H₄OCF₃-3 4-Me — 1-202NHCO₂CH₂CH₂OCH₂Ph 4-Me — 1-203 NHCO₂CH₂CH₂OCH₂CH₂Ph 4-Me — 1-204NHCO₂(1,1-dimethyl-3- 4-Me — phenyl-2-pentynyl) 1-205 NHCO₂(CH₂)₄SMe4-Me — 1-206 NHCO₂(CH₂)₄SCF₃ 4-Me — 1-207 NHCO₂(CH₂)₄SPh 4-Me — 1-208NHCO₂(CH₂)₄SOMe 4-Me — 1-209 NHCO₂(CH₂)₄SOCF₃ 4-Me — 1-210NHCO₂(CH₂)₄SOPh 4-Me — 1-211 NHCO₂(CH₂)₄SO₂Me 4-Me — 1-212NHCO₂(CH₂)₄SO₂CF₃ 4-Me — 1-213 NHCO₂(CH₂)₄SO₂Ph 4-Me — 1-214 NHCO₂Ph4-Me — 1-215 NHCO₂C₆H₄OMe-4 4-Me — 1-216 NHCONHMe 4-Me — 1-217NHCONHC₂H₅ 4-Me — 1-218 NHCONHPr-n 4-Me — 1-219 NHCONHBu-t 4-Me — 1-220NHCONHBu-s 4-Me — 1-221 NHCONH(Hex-n) 4-Me — 1-222 H 4-Cl — 1-223 NH₂4-Cl — 1-224 NHCHO 4-Cl — 1-225 NHCOCH₂CF₃ 4-Cl — 1-226 NHCOC₂F₅ 4-Cl —1-227 NHCOCH₂CH₂F 4-Cl — 1-228 NHCOC(CH₃)₂CF₃ 4-Cl — 1-229 NHCOCH₂CH₂CF₃4-Cl — 1-230 NHCOCH₂C₂F₅ 4-Cl — 1-231 NHCOCH₂CH═CH₂ 4-Cl — 1-232NHCOCH₂CH═CMe₂ 4-Cl — 1-233 NHCOC(CH₃)₂CH═CH₂ 4-Cl — 1-234NHCOC(CH₃)₂CH═CHCH₃ 4-Cl — 1-235 NHCOCH₂CH═CHCl 4-Cl — 1-236NHCOCH₂CH═CHCF₃ 4-Cl — 1-237 NHCOCH₂CI═CI₂ 4-Cl — 1-238NHCO(1,1-dimethyl-2- 4-Cl — propynyl) 1-239 NHCO(2-butynyl) 4-Cl — 1-240NHCO(1,1-dimethyl-2- 4-Cl — butynyl) 1-241 NHCO(1,1-dimethyl-2- 4-Cl —pentynyl) 1-242 NHCO(1-propynyl) 4-Cl — 1-243 NHCO(1,1-dimethyl-3-Iodo-4-Cl — 2-pentynyl) 1-244 NHCO(4,4,4-trifluoro-2- 4-Cl — butynyl) 1-245NHCOPr-c 4-Cl — 1-246 NHCOHex-c 4-Cl — 1-247 NHCO(CH₂)₄CO₂H 4-Cl — 1-248NHCOCH₂CH₂NHCO₂Bu-t 4-Cl — 1-249 NHCOCH₂CH₂NHCO₂Et 4-Cl — 1-250NHCOCH₂CH₂CH₂NHCOCH₃ 4-Cl — 1-251 NHCOCH₂CH₂CH₂NHMe 4-Cl — 1-252NHCOCH₂CH₂N(Me)COCH₃ 4-Cl — 1-253 NHCOCH₂CH₂NHCOPh 4-Cl — 1-254NHCOCH₂CH₂N(Me)COPh 4-Cl — 1-255 NHCOCH₂CH₂NHPh 4-Cl — 1-256NHCO(CH₂)₄NH₂ 4-Cl — 1-257 NHCOCH₂NHCH₂Ph 4-Cl — 1-258NHCOCH₂N(CH₂Ph)(CO₂Bu-t) 4-Cl — 1-259 NHCOCH₂CH₂OC₆H₄Cl-4 4-Cl — 1-260NHCOCH₂OPh 4-Cl — 1-261 NHCOCH₂OC₆H₄F-3 4-Cl — 1-262 NHCOCH₂OC₆H₄OCF₃-34-Cl — 1-263 NHCO(CH₂)₄SMe 4-Cl — 1-264 NHCOCH₂CH₂OEt 4-Cl — 1-265NHCOCH₂CH₂OPr-i 4-Cl — 1-266 NHCOCH₂CH₂OBu-i 4-Cl — 1-267NHCOCH₂CH₂OCH₂CH₂OMe 4-Cl — 1-268 NHCO₂CH₃ 4-Cl — 1-269 NHCO₂C₂H₅ 4-Cl —1-270 NHCO₂Pr-n 4-Cl — 1-271 NHCO₂Pr-i 4-Cl — 1-272 NHCO₂Bu-n 4-Cl —1-273 NHCO₂Bu-i 4-Cl — 1-274 NHCO₂Bu-s 4-Cl — 1-275 NHCO₂Bu-t 4-Cl —1-276 NHCO₂Bu-t 5-Br — 58-61 1-277 NHCO₂Bu-t 5-Cl — 38-41 1-278NHCO₂Bu-t 4-Br — 1-279 NHCO₂Bu-t 4-Cl 2-Cl 1-280 NHCO₂Bu-t 4-Cl 3-Cl1-281 NHCO₂Bu-t 4-Cl 4-Cl 1-282 NHCO₂Bu-t 4-Cl 2,4-Cl₂ 1-283 NHCO₂Bu-t4-Cl 3,5-Cl₂ 1-284 NHCO₂Bu-t 4-Cl 3,4,5- Cl₃ 1-285 NHCO₂Bu-t 4-Cl 2-Me1-286 NHCO₂CH₂CF₃ 4-Cl — 1-287 NHCO₂C₂F₅ 4-Cl — 1-288 NHCO₂CH₂CH₂F 4-Cl— 1-289 NHCO₂C(CH₃)₂CF₃ 4-Cl — 1-290 NHCO₂CH₂CH₂CF₃ 4-Cl — 1-291NHCO₂CH₂C₂F₅ 4-Cl — 1-292 NHCO₂CH₂CH═CH₂ 4-Cl — 1-293 NHCO₂CH₂CH═CMe₂4-Cl — 1-294 NHCO₂C(CH₃)₂CH═CH₂ 4-Cl — 1-295 NHCO₂C(CH₃)₂CH═CHCH₃ 4-Cl —1-296 NHCO₂CH₂CH═CHCl 4-Cl — 1-297 NHCO₂CH₂CH═CHCF₃ 4-Cl — 1-298NHCO₂CH₂CI═CI₂ 4-Cl — 1-299 NHCO₂(1,1-dimethyl-2- 4-Cl — propynyl) 1-300NHCO₂(2-butynyl) 4-Cl — 1-301 NHCO₂(1,1-dimethyl-2- 4-Cl — butynyl)1-302 NHCO₂(1,1-dimethyl-2- 4-Cl — pentynyl) — 1-303 NHCO₂(1-propynyl)4-Cl — 1-304 NHCO₂(1,1-dimethyl-3-Iodo- 4-Cl — 2-pentynyl) 1-305NHCO₂(4,4,4-trifluoro-2- 4-Cl — butynyl) 1-306 NHCO₂Pr-c 4-Cl — 1-307NHCO₂Hex-c 4-Cl — 1-308 NHCO₂CH₂CH₂NHCO₂Bu-t 4-Cl — 1-309NHCO₂CH₂CH₂NHCO₂Et 4-Cl — 1-310 NHCO₂CH₂CH₂CH₂NHCOCH₃ 4-Cl — 1-311NHCO₂CH₂CH₂CH₂NMe₂ 4-Cl — 1-312 NHCO₂CH₂CH₂N(Me)COCH₃ 4-Cl — 1-313NHCO₂CH₂CH₂NHCOPh 4-Cl — 1-314 NHCO₂CH₂CH₂N(Me)COPh 4-Cl — 1-315NHCO₂CH₂CH₂NHPh 4-Cl — 1-316 NHCO₂(CH₂)₄NH₂ 4-Cl — 1-317 NHCO₂CH₂NHCH₂Ph4-Cl — 1-318 NHCO₂CH₂N(CH₂Ph)(CO₂Bu-t) 4-Cl — 1-319 NHCO₂CH₂C₃H₅-c 4-Cl— 1-320 NHCO₂CH(CH₃)C₃H₅-c 4-Cl — 1-321 NHCO₂CH₂C₆H₁₁-c 4-Cl — 1-322NHCO₂CH₂Ph 4-Cl — 1-323 NHCO₂CH₂Ph 5-Cl — 109- 110 1-324NHCO₂CH(CH₃)CH₂Ph 4-Cl — 1-325 NHCO₂CH(CH₃)Ph 4-Cl — 1-326NHCO₂C(CH₃)₂Ph 4-Cl — 1-327 NHCO₂CH₂C₆H₄CF₃-4 4-Cl — 1-328NHCO₂CH₂C₆H₄CN-4 4-Cl — 1-329 NHCO₂CH₂C₆H₄CN-3 4-Cl — 1-330NHCO₂CH₂C₆H₄Cl-4 4-Cl — 1-331 NHCO₂CH₂C₆H₄Cl-3 4-Cl — 1-332NHCO₂CH₂C₆H₄OMe-3 4-Cl — 1-333 NHCO₂CH₂C₆H₄OMe-2 4-Cl — 1-334NHCO₂CH₂C₆H₄Me-4 4-Cl — 1-335 NHCO₂CH₂C₆H₄Me-3 4-Cl — 1-336NHCO₂CH₂C₆H₄Me-2 4-Cl — 1-337 NHCO₂CH₂C₆H₄SO₂Me-4 4-Cl — 1-338NHCO₂CH₂C₆H₄SO₂Me-3 4-Cl — 1-339 NHCO₂CH₂C₆H₄Ph-4 4-Cl — 1-340NHCO₂CH₂C₆H₄Ph-3 4-Cl — 1-341 NHCO₂CH₂Py-2 4-Cl — 1-342NHCO₂CH₂(6-Me-2-Py) 4-Cl — 1-343 NHCO₂C(CH₃)₂Py-4 4-Cl — 1-344NHCO₂CH₂(2-thiazolyl) 4-Cl — 1-345 NHCO₂CH₂(2-benzthiazolyl) 4-Cl —1-346 NHCO₂CH₂CH₂OMe 4-Cl — 1-347 NHCO₂CH₂CH₂OEt 4-Cl — 1-348NHCO₂CH₂CH₂OPr-i 4-Cl — 1-349 NHCO₂CH₂CH₂OBu-i 4-Cl — 1-350NHCO₂CH₂CH₂OCH₂CH₂OMe 4-Cl — 1-351 NHCO₂CH₂CH₂OC₆H₄Cl-4 4-Cl — 1-352NHCOCH₂OPh 4-Cl — 1-353 NHCOCH₂OC₆H₄F-3 4-Cl — 1-354 NHCOCH₂OC₆H₄OCF₃-34-Cl — 1-355 NHCO₂CH₂CH₂OCH₂Ph 4-Cl — 1-356 NHCO₂(1,1-dimethyl-3- 4-Cl —phenyl-2-pentynyl) 1-357 NHCO₂CH₂CH₂OCH₂CH₂Ph 4-Cl — 1-358NHCO₂(1,1-dimethyl-3- 4-Cl — phenyl-2-pentynyl) 1-359 NHCO₂(CH₂)₄SMe4-Cl — 1-360 NHCO₂(CH₂)₄SCF₃ 4-Cl — 1-361 NHCO₂(CH₂)₄SPh 4-Cl — 1-362NHCO₂(CH₂)₄SOMe 4-Cl — 1-363 NHCO₂(CH₂)₄SOCF₃ 4-Cl — 1-364NHCO₂(CH₂)₄SOPh 4-Cl — 1-365 NHCO₂(CH₂)₄SO₂Me 4-Cl — 1-366NHCO₂(CH₂)₄SO₂CF₃ 4-Cl — 1-367 NHCO₂(CH₂)₄SOCF₃ 4-Cl — 1-368 NHCO₂Ph4-Cl — 1-369 NHCO₂C₆H₄OMe-4 4-Cl — 1-370 NHCONHMe 4-Cl — 1-371NHCONHC₂H₅ 4-Cl — 1-372 NHCONHPr-n 4-Cl — 1-373 NHCONHBu-t 4-Cl — 1-374NHCONHBu-s 4-Cl — 1-375 NHCONH(Hex-n) 4-Cl — 1-376 NHCOCH₂CF₃ — — 1-377NHCOC₂F₅ — — 1-378 NHCOCH₂CH₂F — — 1-379 NHCOC(CH₃)₂CF₃ — — 1-380NHCOCH₂CH₂CF₃ — — 107- 109 1-381 NHCOCH₂C₂F₅ — — 1-382 NHCOCH₂CH═CH₂ — —1-383 NHCOCH₂CH═CMe₂ — — 1-384 NHCOC(CH₃)₂CH═CH₂ — — 1-385NHCOC(CH₃)₂CH═CHCH₃ — — 1-386 NHCOCH₂CH═CHCl — — 1-387 NHCOCH₂CH═CHCF₃ —— 1-388 NHCOCH₂CI═CI₂ — — 1-389 NHCO(1,1-dimethyl-2- — — propynyl) 1-390NHCO(2-butynyl) — — 1-391 NHCO(1,1-dimethyl-2- — — butynyl) 1-392NHCO(1,1-dimethyl-2- — — pentynyl) 1-393 NHCO(1-propynyl) — — 193- 1941-394 NHCO(1,1-dimethyl-3-Iodo- — — 2-pentynyl) 1-395NHCO(4,4,4-trifluoro-2- — — butynyl) 1-396 NHCO(CH₂)₄CO₂H — — 127- 1291-397 NHCOCH₂CH₂CH₂NHMe₂ — — 1-398 NHCO(CH₂)₄NH₂ — — 1-399NHCOCH₂NHCH₂Ph — — 1-400 NHCOCH₂N(CH₂Ph)(CO₂Bu-t) — — 1-401NHCOCH₂CH₂NMe₂ — — 1-402 NHCOCH₂CH₂NHEt — — 1-403 NHCOCH₂CH₂NHPr-n — —1-404 NHCOCH₂CH₂OC₆H₄Cl-4 — — 1-405 NHCOCH₂OPh — — 1-406 NHCOCH₂OC₆H₄F-3— — 108- 112 1-407 NHCOCH₂OC₆H₄OCF₃-3 — — 128- 129 1-408NHCOCH₂OC₆H₄CN-2 — — 198- 200 1-409 NHCOCH₂OC₆H₄F-4 — — 86-87 1-410NHCOCH₂OC₆H₃(3,4- — — 110- methylenedioxy) 114 1-411NHCOCH₂OC₆H₄(CONH₂)-2 — — 1-412 NHCOCH₂OC₆H₃(3,4-(OCH₃)₂) — — 1-413NHCOCH₂O(6-CF₃-pyrimidin- — — 4-yl) 1-414 NHCOCH₂O(3-Py) — — oil 1-415NHCO₂CH₂CF₃ — — 1-416 NHCO₂C₂F₅ — — 1-417 NHCO₂CH₂CH₂F — — 1-418NHCO₂C(CH₃)₂CF₃ — — 1-419 NHCO₂CH₂CH₂CF₃ — — 1-420 NHCO₂CH₂C₂F₅ — —1-421 NHCO₂CH₂CH═CH₂ — — 1-422 NHCO₂CH₂CH═CMe₂ — — 1-423NHCO₂C(CH₃)₂CH═CH₂ — — 1-424 NHCO₂C(CH₃)₂CH═CHCH₃ — — 1-425NHCO₂CH₂CH═CHCl — — 1-426 NHCO₂CH₂CH═CHCF₃ — — 1-427 NHCO₂CH₂CI═CI₂ — —1-428 NHCO₂(1,1-dimethyl-2- — — propynyl) 1-429 NHCO₂(2-butynyl) — —37-39 1-430 NHCO₂(1,1-dimethyl-2- — — butynyl) 1-431NHCO₂(1,1-dimethyl-2- — — pentynyl) 1-432 NHCO₂(1-propynyl) — — 1-433NHCO₂(1,1-dimethyl-3-Iodo- — — 2-pentynyl) 1-434NHCO₂(4,4,4-trifluoro-2- — — butynyl) 1-435 NHCO₂(1,1-dimethyl-3- — —phenyl-2-pentynyl) 1-436 NHCO₂CH₂CH₂NHCO₂Bu-t — — 115- 117 1-437NHCO₂CH₂CH₂NHCO₂Et — — 1-438 NHCO₂CH₂N(CH₂Ph)(CO₂Bu-t) — — 1-439NHCO₂CH₂NCH₂Ph — — 1-440 NHCO₂CH₂CH₂NCH₂Ph — — 1-441NHCO₂CH₂CH₂NCH₂C₆H₄Cl-4 — — 1-442 NHCO₂CH₂CH₂NHMe — — 1-443NHCO₂CH₂C(CH₃)₂N(CH₃)₂ — — 1-444 NHCO₂CH(CH₃)CH₂N(CH₃)₂ — — 1-445NHCO₂CH₂C₃H₅-c — — 1-446 NHCO₂CH(CH₃)C₃H₅-c — — 1-447 NHCO₂CH₂C₆H₁₁-c —— 44-47 1-448 NHCO₂CH(CH₃)CH₂Ph — — 1-449 NHCO₂CH(CH₃)Ph — — 1-450NHCO₂C(CH₃)₂Ph — — 1-451 NHCO₂CH₂C₆H₄CF₃-4 — — 1-452 NHCO₂CH₂C₆H₄CN-4 —— 55-59 1-453 NHCO₂CH₂C₆H₄CN-3 — — 45-48 1-454 NHCO₂CH₂C₆H₄Cl-4 — —47-49 1-455 NHCO₂CH₂C₆H₄Cl-3 — — 39-44 1-456 NHCO₂CH₂C₆H₄OMe-3 — — 1-457NHCO₂CH₂C₆H₄OMe-2 — — 1-458 NHCO₂CH₂C₆H₄Me-4 — — 40-45 1-459NHCO₂CH₂C₆H₄Me-3 — — 46-49 1-460 NHCO₂CH₂C₆H₄Me-2 — — 57-60 1-461NHCO₂CH₂C₆H₄SO₂Me-4 — — 66-70 1-462 NHCO₂CH₂C₆H₄SO₂Me-3 — — 45-50 1-463NHCO₂CH₂C₆H₄Ph-4 — — 60-64 1-464 NHCO₂CH₂C₆H₄Ph-3 — — 59-63 1-465NHCO₂CH₂C₆H₄OCH₃-4 — — 1-466 NHCO₂CH₂C₆H₃(3,4- — — methylenedioxy) 1-467NHCO₂CH₂Py-2 — — 1-468 NHCO₂CH₂(6-Me-2-Py) — — 94-96 1-469NHCO₂C(CH₃)₂Py-4 — — 168- 169 1-470 NHCO₂CH₂(2-thiazolyl) — — 1-471NHCO₂CH₂(2-benzthiazolyl) — — 1-472 NHCO₂CH₂(3-Py) — — 140- 141 1-473NHCO₂CH₂(4-Py) — — 52-55 1-474 NHCO₂CH(CH₃)(4-Py) — — 1-475NHCO₂CH₂CH₂OMe — — 81-82 1-476 NHCO₂CH₂CH₂OEt — — 89-91 1-477NHCO₂CH₂CH₂OPr-i — — 1-478 NHCO₂CH₂CH₂OBu-i — — 93-94 1-479NHCO₂CH₂CH₂OCH₂CH₂OMe — — 115- 117 1-480 NHCO₂C(CH₃)₂CH₂OCH₃ — — 1-481NHCO₂CH(CH₃)CH₂OCH₃ — — 1-482 NHCO₂CH₂CH₂OC₆H₄Cl-4 — — 1-483 NHCO₂CH₂OPh— — 1-484 NHCO₂CH₂OC₆H₄F-3 — — 1-485 NHCO₂CH₂OC₆H₄OCF₃-3 — — 1-486NHCO₂CH₂CH₂OCH₂Ph — — 1-487 NHCO₂CH₂CH₂OCH₂CH₂Ph — — 1-488NHCO₂(CH₂)₄SMe — — 1-489 NHCO₂(CH₂)₄SCF₃ — — 1-490 NHCO₂(CH₂)₄SPh — —1-491 NHCO₂(CH₂)₄SOMe — — 1-492 NHCO₂(CH₂)₄SOCF₃ — — 1-493NHCO₂(CH₂)₄SOPh — — 1-494 NHCO₂(CH₂)₄SO₂Me — — 123- 124 1-495NHCO₂(CH₂)₄SO₂CF₃ — — 1-496 NHCO₂(CH₂)₄SO₂Ph — — 1-497 NHCO₂Ph — — 129-131 1-498 NHCO₂C₆H₄OMe-4 — — 179- 181 1-499 NHCOCH₂CH₂CH₂COCH₃ — —

TABLE 2

mp No Z¹¹ R¹¹ (X)_(n1) ° C. 2-1 H Me — 2-2 NH₂ Me — 2-3 NH₂ Bu-t — 2-4NH₂ OC₂H₅ — 2-5 NH₂ OCH₃ — 2-6 NH₂ C₂H₅ — 2-7 NHCHO Me — 2-8 NHCOCH₃ Me— 2-9 NHCOC₂H₅ Me — 2-10 NHCOPr-n Me — 2-11 NHCOPr-i Me — 2-12 NHCOBu-nMe — 2-13 NHCOBu-i Me — 2-14 NHCOBu-s Me — 2-15 NHCOBu-t Me — 2-16NHCOBu-t OMe — 2-17 NHCOCH₂CF₃ Me — 2-18 NHCOC₂F₅ Me — 2-19 NHCOCH₂CH₂FMe — 2-20 NHCOC(CH₃)₂CF₃ Me — 2-21 NHCOCH₂CH₂CF₃ Me — 2-22 NHCOCH₂C₂F₅Me — 2-23 NHCOCH₂CH═CH₂ Me — 2-24 NHCOCH₂CH═CMe₂ Me — 2-25NHCOC(CH₃)₂CH═CH₂ Me — 2-26 NHCOC(CH₃)₂CH═CHCH₃ Me — 2-27 NHCOCH₂CH═CHClMe — 2-28 NHCOCH₂CH═CHCF₃ Me — 2-29 NHCOCH₂CI═CI₂ Me — 2-30NHCO(1,1-dimethyl-2- Me — propynyl) 2-31 NHCO(2-butynyl) Me — 2-32NHCO(1,1-dimethyl-2- Me — butynyl) 2-33 NHCO(1,1-dimethyl-2- Me —pentynyl) 2-34 NHCO(1-propynyl) Me — 2-35 NHCO(1,1-dimethyl-3-Iodo- Me —2-pentynyl) 2-36 NHCO(4,4,4-trifluoro-2- Me — butynyl) 2-37 NHCOPr-c Me— 2-38 NHCOHex-c Me — 2-39 NHCO(CH₂)₄CO₂H Me — 2-40 NHCOCH₂CH₂NHCO₂Bu-tMe — 2-41 NHCOCH₂CH₂NHCO₂Et Me — 2-42 NHCOCH₂CH₂CH₂NHCOCH₃ Me — 2-43NHCOCH₂CH₂CH₂NHMe₂ Me — 2-44 NHCOCH₂CH₂N(Me)COCH₃ Me — 2-45NHCOCH₂CH₂NHCOPh Me — 2-46 NHCOCH₂CH₂N(Me)COPh Me — 2-47 NHCOCH₂CH₂NHPhMe — 2-48 NHCO(CH₂)₄NH₂ Me — 2-49 NHCOCH₂NHCH₂Ph Me — 2-50NHCOCH₂N(CH₂Ph)(CO₂Bu-t) Me — 2-51 NHCOCH₂CH₂OCH₄Cl-4 Me — 2-52NHCOCH₂OPh Me — 2-53 NHCOCH₂OC₆H₄F-3 Me — 2-54 NHCOCH₂OC₆H₄OCF₃-3 Me —2-55 NHCO(CH₂)₄SMe Me — 2-56 NHCOCH₂CH₂OEt Me — 2-57 NHCOCH₂CH₂OPr-i Me— 2-58 NHCOCH₂CH₂OBu-i Me — 2-59 NHCOCH₂CH₂OCH₂CH₂OMe Me — 2-60 NHCO₂CH₃Me — 2-61 NHCO₂C₂H₅ Me — 2-62 NHCO₂Pr-n Me — 2-63 NHCO₂Pr-i Me — 2-64NHCO₂Bu-n Me — 2-65 NHCO₂Bu-i Me — 2-66 NHCO₂Bu-s Me — 2-67 NHCO₂Bu-ti-Pr — 2-68 NHCO₂Bu-t Me — 2-69 NHCO₂Bu-t t-Bu — 2-70 NHCO₂Bu-t Et —2-71 NHCO₂Bu-t CH═CH2 — 2-72 NHCO₂Bu-t OMe — 2-73 NHCO₂Bu-t OEt — 2-74NHCO₂Bu-t OCH₂CH₂OEt — 2-75 NHCO₂Bu-t OPr-i — 2-76 NHCO₂Bu-t OBu-n —2-77 NHCO₂Bu-t SMe — 2-78 NHCO₂Bu-t SOMe — 2-79 NHCO₂Bu-t SO₂Me — 2-80NHCO₂Bu-t NMe₂ — 2-81 NHCO₂Bu-t N(Me)(CO₂Bu-t) — 2-82 NHCO₂Bu-t CN —2-83 NHCO₂Bu-t morphorino — 2-84 NHCO₂Bu-t Ph — 2-85 NHCO₂Bu-t CO₂C₂H₅ —2-86 NHCO₂Bu-t CONHCH₃ — 2-87 NHCO₂Bu-t CF₃ — 2-88 NHCO₂Bu-t OH — 2-89NHCO₂Bu-t SH — 2-90 NHCO₂Bu-t CH₂CI═CI₂ — 2-91 NHCO₂Bu-t etynyl — 2-92NHCO₂Bu-t propargyl — 2-93 NHCO₂Bu-t (3-iodo-2- — propynyl) 2-94NHCO₂Bu-t Ph — 2-95 NHCO₂Bu-t C₆H₄OMe-4 — 2-96 NHCO₂Bu-t 2-pyridyl —2-97 NHCO₂Bu-t 4-CF₃-2-oxazolyl — 2-98 NHCO₂Bu-t 3-CF₃-5-Cl-2- — pyridyl2-99 NHCO₂Bu-t pyrrolidino — 2-100 NHCO₂Bu-t COMe — 2-101 NHCO₂Bu-tCONHMe — 2-102 NHCO₂Bu-t CONMe₂ — 2-103 NHCO₂Bu-t COPr-c — 2-104NHCO₂Bu-t COPh — 2-105 NHCO₂Bu-t COCH₂CH═CH₂ — 2-106 NHCO₂Bu-tCO(propargyl) — 2-107 NHCO₂Bu-t CO₂Me — 2-108 NHCO₂Bu-t CO₂Ph — 2-109NHCO₂Bu-t CO₂CH₂CH═CH₂ — 2-110 NHCO₂Bu-t CO₂(propargyl) — 2-111NHCO₂Bu-t Me 2-Cl 2-112 NHCO₂Bu-t Me 3-Cl 2-113 NHCO₂Bu-t Me 4-Cl 2-114NHCO₂Bu-t Me 2,4-Cl₂ 2-115 NHCO₂Bu-t Me 3,5-Cl₂ 2-116 NHCO₂Bu-t Me3,4,5-Cl₃ 2-117 NHCO₂Bu-t Me 2-Me 2-118 NHCO₂Bu-n NH₂ — 2-119 NHCO₂Bu-nNHCO₂Bu-t — 2-120 NHCO₂CH₂CF₃ Me — 2-121 NHCO₂C₂F₅ Me — 2-122NHCO₂CH₂CH₂F Me — 2-123 NHCO₂C(CH₃)₂CF₃ Me — 2-124 NHCO₂CH₂CH₂CF₃ Me —2-125 NHCO₂CH₂C₂F₅ Me — 2-126 NHCO₂CH₂CH═CH₂ Me — 2-127 NHCO₂CH₂CH═CMe₂Me — 2-128 NHCO₂C(CH₃)₂CH═CH₂ Me — 2-129 NHCO₂C(CH₃)₂CH═CHCH₃ Me — 2-130NHCO₂CH₂CH═CHCl Me — 2-131 NHCO₂CH₂CH═CHCF₃ Me — 2-132 NHCO₂CH₂CI═CI₂ Me— 2-133 NHCO₂(1,1-dimethyl-2- Me — propynyl) 2-134 NHCO₂(2-butynyl) Me —2-135 NHCO₂(1,1-dimethyl-2- Me — butynyl) 2-136 NHCO₂(1,1-dimethyl-2- Me— pentynyl) 2-137 NHCO₂(1-propynyl) Me — 2-138NHCO₂(1,1-dimethyl-3-Iodo- Me — 2-pentynyl) 2-139NHCO₂(4,4,4-trifluoro-2- Me — butynyl) 2-140 NHCO₂Pr-c Me — 2-141NHCO₂Hex-c Me — 2-142 NHCO₂CH₂CH₂NHCO₂Bu-t Me — 2-143 NHCO₂CH₂CH₂NHCO₂EtMe — 2-144 NHCO₂CH₂CH₂CH₂NHCOCH₃ Me — 2-145 NHCO₂CH₂CH₂CH₂NHMe₂ Me —2-146 NHCO₂CH₂CH(Me)COCH₃ Me — 2-147 NHCO₂CH₂CH₂NHCOPh Me — 2-148NHCO₂CH₂CH₂N(Me)COPh Me — 2-149 NHCO₂CH₂CH₂NHPh Me — 2-150NHCO₂(CH₂)₄NH₂ Me — 2-151 NHCO₂CH₂NHCH₂Ph Me — 2-152NHCO₂CH₂N(CH₂Ph)(CO₂Bu-t) Me — 2-153 NHCO₂CH₂C₃H₅-c Me — 2-154NHCO₂CH(CH₃)C₃H₅-c Me — 2-155 NHCO₂CH₂C₆H₁₁-c Me — 2-156 NHCO₂CH₂Ph Me —2-157 NHCO₂CH(CH₃)CH₂Ph Me — 2-158 NHCO₂CH(CH₃)Ph Me — 2-159NHCO₂C(CH₃)₂Ph Me — 2-160 NHCO₂CH₂C₆H₄CF₃-4 Me — 2-161 NHCO₂CH₂C₆H₄CN-4Me — 2-162 NHCO₂CH₂C₆H₄CN-3 Me — 2-163 NHCO₂CH₂C₆H₄Cl-4 Me — 2-164NHCO₂CH₂C₆H₄Cl-3 Me — 2-165 NHCO₂CH₂C₆H₄OMe-3 Me — 2-166NHCO₂CH₂C₆H₄OMe-2 Me — 2-167 NHCO₂CH₂C₆H₄Me-4 Me — 2-168NHCO₂CH₂C₆H₄Me-3 Me — 2-169 NHCO₂CH₂C₆H₄Me-2 Me — 2-170NHCO₂CH₂C₆H₄SO₂Me-4 Me — 2-171 NHCO₂CH₂C₆H₄SO₂Me-3 Me — 2-172NHCO₂CH₂C₆H₄Ph-4 Me — 2-173 NHCO₂CH₂C₆H₄Ph-3 Me — 2-174 NHCO₂CH₂Py-2 Me— 2-175 NHCO₂CH₂(6-Me-2-Py) Me — 2-176 NHCO₂C(CH₃)₂Py-4 Me — 2-177NHCO₂CH₂(2-thiazolyl) Me — 2-178 NHCO₂CH₂(2-benzthiazolyl) Me — 2-179NHCO₂CH₂CH₂OMe Me — 2-180 NHCO₂CH₂CH₂OEt Me — 2-181 NHCO₂CH₂CH₂OPr-i Me— 2-182 NHCO₂CH₂CH₂OBu-i Me — 2-183 NHCO₂CH₂CH₂OCH₂CH₂OMe Me — 2-184NHCO₂CH₂CH₂OEt i-Pr — 2-185 NHCO₂CH₂CH₂OC₆H₄Cl-4 Me — 2-186 NHCOCH₂OPhMe — 2-187 NHCOCH₂OC₆H₄F-3 Me — 2-188 NHCOCH₂OC₆H₄OCF₃-3 Me — 2-189NHCO₂CH₂CH₂OCH₂Ph Me — 2-190 NHCO₂CH₂CH₂OCH₂CH₂Ph Me — 2-191NHCO₂(1,1-dimethyl-3- Me — phenyl-2-pentynyl) 2-192 NHCO₂(CH₂)₄SMe Me —2-193 NHCO₂(CH₂)₄SCF₃ Me — 2-194 NHCO₂(CH₂)₄SPh Me — 2-195NHCO₂(CH₂)₄SOMe Me — 2-196 NHCO₂(CH₂)₄SOCF₃ Me — 2-197 NHCO₂(CH₂)₄SOPhMe — 2-198 NHCO₂(CH₂)₄SO₂Me Me — 2-199 NHCO₂(CH₂)₄SO₂CF₃ Me — 2-200NHCO₂(CH₂)₄SO₂Ph Me — 2-201 NHCO₂Ph Me — 2-202 NHCO₂C₆H₄OMe-4 Me — 2-203NHCONHMe Me — 2-204 NHCONHC₂H₅ Me — 2-205 NHCONHPr-n Me — 2-206NHCONHBu-t Me — 2-207 NHCONHBu-s Me — 2-208 NHCONH(Hex-n) Me — 2-209 HCl — 2-210 NH₂ Cl — 2-211 NHCHO Cl — 2-212 NHCOCH₂CF₃ Cl — 2-213NHCOC₂F₅ Cl — 2-214 NHCOCH₂CH₂F Cl — 2-215 NHCOC(CH₃)₂CF₃ Cl — 2-216NHCOCH₂CH₂CF₃ Cl — 2-217 NHCOCH₂C₂F₅ Cl — 2-218 NHCOCH₂CH═CH₂ Cl — 2-219NHCOCH₂CH═CMe₂ Cl — 2-220 NHCOC(CH₃)₂CH═CH₂ Cl — 2-221NHCOC(CH₃)₂CH═CHCH₃ Cl — 2-222 NHCOCH₂CH═CHCl Cl — 2-223 NHCOCH₂CH═CHCF₃Cl — 2-224 NHCOCH₂CI═CI₂ Cl — 2-225 NHCO(1,1-dimethyl-2- Cl — propynyl)2-226 NHCO(2-butynyl) Cl — 2-227 NHCO(1,1-dimethyl-2- Cl — butynyl)2-228 NHCO(1,1-dimethyl-2- Cl — pentynyl) 2-229 NHCO(1-propynyl) Cl —2-230 NHCO(1,1-dimethyl-3-Iodo- Cl — 2-pentynyl) 2-231NHCO(4,4,4-trifluoro-2- Cl — butynyl) 2-232 NHCOPr-c Cl — 2-233NHCOHex-c Cl — 2-234 NHCO(CH₂)₄CO₂H Cl — 2-235 NHCOCH₂CH₂NHCO₂Bu-t Cl —2-236 NHCOCH₂CH₂NHCO₂Et Cl — 2-237 NHCOCH₂CH₂CH₂NHCOCH₃ Cl — 2-238NHCOCH₂CH₂CH₂NHMe₂ Cl — 2-239 NHCOCH₂CH₂N(Me)COCH₃ Cl — 2-240NHCOCH₂CH₂NHCOPh Cl — 2-241 NHCOCH₂CH₂N(Me)COPh Cl — 2-242NHCOCH₂CH₂NHPh Cl — 2-243 NHCO(CH₂)₄NH₂ Cl — 2-244 NHCOCH₂NHCH₂Ph Cl —2-245 NHCOCH₂N(CH₂Ph)(CO₂Bu-t) Cl — 2-246 NHCOCH₂CH₂OC₆H₄Cl-4 Cl — 2-247NHCOCH₂OPh Cl — 2-248 NHCOCH₂OC₆H₄F-3 Cl — 2-249 NHCOCH₂OC₆H₄OCF₃-3 Cl —2-250 NHCO(CH₂)₄SMe Cl — 2-251 NHCOCH₂CH₂OEt Cl — 2-252 NHCOCH₂CH₂OPr-iCl — 2-253 NHCOCH₂CH₂OBu-i Cl — 2-254 NHCOCH₂CH₂OCH₂CH₂OMe Cl — 2-255NHCO₂CH₃ Cl — 2-256 NHCO₂C₂H₅ Cl — 2-257 NHCO₂Pr-n Cl — 2-258 NHCO₂Pr-iCl — 2-259 NHCO₂Bu-n Cl — 2-260 NHCO₂Bu-i Cl — 2-261 NHCO₂Bu-s Cl —2-262 NHCO₂Bu-t Cl — 2-263 NHCO₂Bu-t Br — 91-93 2-264 NHCO₂Bu-t Cl 2-Cl2-265 NHCO₂Bu-t Cl 3-Cl 2-266 NHCO₂Bu-t Cl 4-Cl 2-267 NHCO₂Bu-t Cl2,4-Cl₂ 2-268 NHCO₂Bu-t Cl 3,5-Cl₂ 2-269 NHCO₂Bu-t Cl 3,4,5-Cl₃ 2-270NHCO₂Bu-t Cl 2-Me 2-271 NHCO₂CH₂CF₃ Cl — 2-272 NHCO₂C₂F₅ Cl — 2-273NHCO₂CH₂CH₂F Cl — 2-274 NHCO₂C(CH₃)₂CF₃ Cl — 2-275 NHCO₂CH₂CH₂CF₃ Cl —2-276 NHCO₂CH₂C₂F₅ Cl — 2-277 NHCO₂CH₂CH═CH₂ Cl — 2-278 NHCO₂CH₂CH═CMe₂Cl — 2-279 NHCO₂C(CH₃)₂CH═CH₂ Cl — 2-280 NHCO₂C(CH₃)₂CH═CHCH₃ Cl — 2-281NHCO₂CH₂CH═CHCl Cl — 2-282 NHCO₂CH₂CH═CHCF₃ Cl — 2-283 NHCO₂CH₂CI═CI₂ Cl— 2-284 NHCO₂(1,1-dimethyl-2- Cl — propynyl) 2-285 NHCO₂(2-butynyl) Cl —2-286 NHCO₂(1,1-dimethyl-2- Cl — butynyl) 2-287 NHCO₂(1,1-dimethyl-2- Cl— pentynyl) 2-288 NHCO₂(1-propynyl) Cl — 2-289NHCO₂(1,1-dimethyl-3-Iodo- Cl — 2-pentynyl) 2-290NHCO₂(4,4,4-trifluoro-2- Cl — butynyl) 2-291 NHCO₂Pr-c Cl — 2-292NHCO₂Hex-c Cl — 2-293 NHCO₂CH₂CH₂NHCO₂Bu-t Cl — 2-294 NHCO₂CH₂CH₂NHCO₂EtCl — 2-295 NHCO₂CH₂CH₂CH₂NHCOCH₃ Cl — 2-296 NHCO₂CH₂CH₂CH₂NMe₂ Cl —2-297 NHCO₂CH₂CH₂N(Me)COCH₃ Cl — 2-298 NHCO₂CH₂CH₂NHCOPh Cl — 2-299NHCO₂CH₂CH₂N(Me)COPh Cl — 2-300 NHCO₂CH₂CH₂NHPh Cl — 2-301NHCO₂(CH₂)₄NH₂ Cl — 2-302 NHCO₂CH₂NHCH₂Ph Cl — 2-303NHCO₂CH₂N(CH₂Ph)(CO₂Bu-t) Cl — 2-304 NHCO₂CH₂C₃H₅-c Cl — 2-305NHCO₂CH(CH₃)C₃H₅-c Cl — 2-306 NHCO₂CH₂C₆H₁₁-c Cl — 2-307 NHCO₂CH₂Ph Cl —2-308 NHCO₂CH(CH₃)CH₂Ph Cl — 2-309 NHCO₂CH(CH₃)Ph Cl — 2-310NHCO₂C(CH₃)₂Ph Cl — 2-311 NHCO₂CH₂C₆H₄CF₃-4 Cl — 2-312 NHCO₂CH₂C₆H₄CN-4Cl — 2-313 NHCO₂CH₂C₆H₄CN-3 Cl — 2-314 NHCO₂CH₂C₆H₄Cl-4 Cl — 2-315NHCO₂CH₂C₆H₄Cl-3 Cl — 2-316 NHCO₂CH₂C₆H₄OMe-3 Cl — 2-317NHCO₂CH₂C₆H₄OMe-2 Cl — 2-318 NHCO₂CH₂C₆H₄Me-4 Cl — 2-319NHCO₂CH₂C₆H₄Me-3 Cl — 2-320 NHCO₂CH₂C₆H₄Me-2 Cl — 2-321NHCO₂CH₂C₆H₄SO₂Me-4 Cl — 2-322 NHCO₂CH₂C₆H₄SO₂Me-3 Cl — 2-323NHCO₂CH₂C₆H₄Ph-4 Cl — 2-324 NHCO₂CH₂C₆H₄Ph-3 Cl — 2-325 NHCO₂CH₂Py-2 Cl— 2-326 NHCO₂CH₂(6-Me-2-Py) Cl — 2-327 NHCO₂C(CH₃)₂Py-4 Cl — 2-328NHCO₂CH₂(2-thiazolyl) Cl — 2-329 NHCO₂CH₂(2-benzthiazolyl) Cl — 2-330NHCO₂CH₂CH₂OMe Cl — 2-331 NHCO₂CH₂CH₂OEt Cl — 2-332 NHCO₂CH₂CH₂OPr-i Cl— 2-333 NHCO₂CH₂CH₂OBu-i Cl — 2-334 NHCO₂CH₂CH₂OCH₂CH₂OMe Cl — 2-335NHCO₂CH₂CH₂OC₆H₄Cl-4 Cl — 2-336 NHCOCH₂OPh Cl — 2-337 NHCOCH₂OC₆H₄F-3 Cl— 2-338 NHCOCH₂OC₆H₄OCF₃-3 Cl — 2-339 NHCO₂CH₂CH₂OCH₂Ph Cl — 2-340NHCO₂(1,1-dimethyl-3- Cl — phenyl-2-pentynyl) 2-341 NHCO₂CH₂CH₂OCH₂CH₂PhCl — 2-342 NHCO₂(1,1-dimethyl-3- Cl — phenyl-2-pentynyl) 2-343NHCO₂(CH₂)₄SMe Cl — 2-344 NHCO₂(CH₂)₄SCF₃ Cl — 2-345 NHCO₂(CH₂)₄SPh Cl —2-346 NHCO₂(CH₂)₄SOMe Cl — 2-347 NHCO₂(CH₂)₄SOCF₃ Cl — 2-348NHCO₂(CH₂)₄SOPh Cl — 2-349 NHCO₂(CH₂)₄SO₂Me Cl — 2-350 NHCO₂(CH₂)₄SO₂CF₃Cl — 2-351 NHCO₂(CH₂)₄SO₂Ph Cl — 2-352 NHCO₂Ph Cl — 2-353 NHCO₂C₆H₄OMe-4Cl — 2-354 NHCONHMe Cl — 2-355 NHCONHC₂H₅ Cl — 2-356 NHCONHPr-n Cl —2-357 NHCONHBu-t Cl — 2-358 NHCONHBu-s Cl — 2-359 NHCONH(Hex-n) Cl —2-360 NHCOCH₂CF₃ — — 2-361 NHCOC₂F₅ — — 2-362 NHCOCH₂CH₂F — — 2-363NHCOC(CH₃)₂CF₃ — — 2-364 NHCOCH₂CH₂CF₃ — — 2-365 NHCOCH₂C₂F₅ — — 2-366NHCOCH₂CH═CH₂ — — 2-367 NHCOCH₂CH═CMe₂ — — 2-368 NHCOC(CH₃)₂CH═CH₂ — —2-369 NHCOC(CH₃)₂CH═CHCH₃ — — 2-370 NHCOCH₂CH═CHCl — — 2-371NHCOCH₂CH═CHCF₃ — — 2-372 NHCOCH₂CI═CI₂ — — 2-373 NHCO(1,1-dimethyl-2- —— propynyl) 2-374 NHCO(2-butynyl) — — 2-375 NHCO(1,1-dimethyl-2- — —butynyl) 2-376 NHCO(1,1-dimethyl-2- — — pentynyl) 2-377 NHCO(1-propynyl)— — 2-378 NHCO(1,1-dimethyl-3-Iodo- — — 2-pentynyl) 2-379NHCO(4,4,4-trifluoro-2- — — butynyl) 2-380 NHCO(CH₂)₄CO₂H — — 2-381NHCOCH₂CH₂CH₂NHMe₂ — — 2-382 NHCO(CH₂)₄NH₂ — — 2-383 NHCOCH₂NHCH₂Ph — —2-384 NHCOCH₂N(CH₂Ph)(CO₂Bu-t) — — 2-385 NHCOCH₂CH₂NMe₂ — — 2-386NHCOCH₂CH₂NHEt — — 2-387 NHCOCH₂CH₂NHPr-n — — 2-388 NHCOCH₂CH₂OC₆H₄Cl-4— — 2-389 NHCOCH₂OPh — — 95-97 2-390 NHCOCH₂OC₆H₄F-3 — — 2-391NHCOCH₂OC₆H₄OCF₃-3 — — 112-113 2-392 NHCOCH2OC₆H₄CN-2 — — 159-162 2-393NHCOCH2OC₆H₄F-4 — — 2-394 NHCOCH₂OC₆H₃(3,4- — — 67-72 methylenedioxy)2-395 NHCOCH₂OC₆H₄(CONH₂)-2 — — 2-396 NHCOCH₂OC₆H₃(3,4-(OCH₃)₂) — —140-141 2-397 NHCOCH₂O(6-CF₃-pyrimidin- — — 108-111 4-yl) (dec.) 2-398NHCOCH₂O(3-Py) — — 2-399 NHCOCH₂CH₂CH₂COCH₃ — — 2-400 NHCO₂CH₂CF₃ — —2-401 NHCO₂C₂F₅ — — 2-402 NHCO₂CH₂CH₂F — — 2-403 NHCO₂C(CH₃)₂CF₃ — —2-404 NHCO₂CH₂CH₂CF₃ — — 2-405 NHCO₂CH₂C₂F₅ — — 2-406 NHCO₂CH₂CH═CH₂ — —2-407 NHCO₂CH₂CH═CMe₂ — — 2-408 NHCO₂C(CH₃)₂CH═CH₂ — — 2-409NHCO₂C(CH₃)₂CH═CHCH₃ — — 2-410 NHCO₂CH₂CH═CHCl — — 2-411NHCO₂CH₂CH═CHCF₃ — — 2-412 NHCO₂CH₂CI═CI₂ — — 2-413NHCO₂(1,1-dimethyl-2- — — propynyl) 2-414 NHCO₂(2-butynyl) — — 2-415NHCO₂(1,1-dimethyl-2- — — butynyl) 2-416 NHCO₂(1,1-dimethyl-2- — —pentynyl) 2-417 NHCO₂(1-propynyl) — — 2-418 NHCO₂(1,1-dimethyl-3-Iodo- —— 2-pentynyl) 2-419 NHCO₂(4,4,4-trifluoro-2- — — butynyl) 2-420NHCO₂(1,1-dimethyl-3- — — phenyl-2-pentynyl) 2-421 NHCO₂CH₂CH₂NHCO₂Bu-t— — 2-422 NHCO₂CH₂CH₂NHCO₂Et — — 2-423 NHCO₂CH₂N(CH₂Ph)(CO₂Bu-t) — —2-424 NHCO₂CH₂NCH₂Ph — — 2-425 NHCO₂CH₂CH₂NCH₂Ph — — 2-426NHCO₂CH₂CH₂NCH₂C₆H₄Cl-4 — — 2-427 NHCO₂CH₂CH₂NHMe — — 2-428NHCO₂CH₂C(CH₃)₂N(CH₃)₂ — — 2-429 NHCO₂CH(CH₃)CH₂N(CH₃)₂ — — 2-430NHCO₂CH₂C₃H₅-c — — 2-431 NHCO₂CH(CH₃)C₃H₅-c — — 2-432 NHCO₂CH₂C₆H₁₁-c —— 2-433 NHCO₂CH(CH₃)CH₂Ph — — 2-434 NHCO₂CH(CH₃)Ph — — 2-435NHCO₂C(CH₃)₂Ph — — 2-436 NHCO₂CH₂C₆H₄CF₃-4 — — 2-437 NHCO₂CH₂C₆H₄CN-4 —— 2-438 NHCO₂CH₂C₆H₄CN-3 — — 2-439 NHCO₂CH₂C₆H₄Cl-4 — — 2-440NHCO₂CH₂C₆H₄Cl-3 — — 2-441 NHCO₂CH₂C₆H₄OMe-3 — — 2-442 NHCO₂CH₂C₆H₄OMe-2— — 2-443 NHCO₂CH₂C₆H₄Me-4 — — 2-444 NHCO₂CH₂C₆H₄Me-3 — — 2-445NHCO₂CH₂C₆H₄Me-2 — — 2-446 NHCO₂CH₂C₆H₄SO₂Me-4 — — 2-447NHCO₂CH₂C₆H₄SO₂Me-3 — — 2-448 NHCO₂CH₂C₆H₄Ph-4 — — 2-449NHCO₂CH₂C₆H₄Ph-3 — — 2-450 NHCO₂CH₂C₆H₄OCH₃-4 — — 2-451NHCO₂CH₂C₆H₃(3,4- methylenedioxy) 2-452 NHCO₂CH₂Py-2 — — 2-453NHCO₂CH₂(6-Me-2-Py) — — 2-454 NHCO₂C(CH₃)₂Py-4 — — 2-455NHCO₂CH₂(2-thiazolyl) — — 2-456 NHCO₂CH₂(2-benzthiazolyl) — — 2-457NHCO₂CH₂(3-Py) — — 2-458 NHCO₂CH₂(4-Py) — — 2-459 NHCO₂CH(CH₃)(4-Py) — —2-460 NHCO₂CH₂CH₂OMe — — 2-461 NHCO₂CH₂CH₂OEt — — 2-462 NHCO₂CH₂CH₂OPr-i— — 2-463 NHCO₂CH₂CH₂OBu-i — — 2-464 NHCO₂CH₂CH₂OCH₂CH₂OMe — — 2-465NHCO₂C(CH₃)₂CH₂OCH₃ — — 2-466 NHCO₂CH(CH₃)CH₂OCH₃ — — 2-467NHCO₂CH₂CH₂OC₆H₄Cl-4 — — 2-468 NHCO₂CH₂OPh — — 2-469 NHCO₂CH₂OC₆H₄F-3 —— 2-470 NHCO₂CH₂OC₆H₄OCF₃-3 — — 2-471 NHCO₂CH₂CH₂OCH₂Ph — — 2-472NHCO₂CH₂CH₂OCH₂CH₂Ph — — 2-473 NHCO₂(CH₂)₄SMe — — 2-474 NHCO₂(CH₂)₄SCF₃— — 2-475 NHCO₂(CH₂)₄SPh — — 2-476 NHCO₂(CH₂)₄SOMe — — 2-477NHCO₂(CH₂)₄SOCF₃ — — 2-478 NHCO₂(CH₂)₄SOPh — — 2-479 NHCO₂(CH₂)₄SO₂Me —— 2-480 NHCO₂(CH₂)₄SO₂CF₃ — — 2-481 NHCO₂(CH₂)₄SO₂Ph — — 2-482 NHCO₂Ph —— 2-483 NHCO₂C₆H₄OMe-4 — —

TABLE 3

mp No Z R_(n2) (X)_(n1) ° C. 3-1 H 4-Me — 3-2 NH₂ 4-Me — 3-3 NH₂ 4-Bu-t— 3-4 NH₂ 4-OC₂H₅ — 3-5 NH₂ 5-CH₃ — 3-6 NH₂ 4-OCH₃ — 3-7 NH₂ 4-C₂H₅ —3-8 NHCHO 4-Me — 3-9 NHCOCH₃ 4-Me — 3-10 NHCOC₂H₅ 4-Me — 3-11 NHCOPr-n4-Me — 3-12 NHCOPr-i 4-Me — 3-13 NHCOBu-n 4-Me — 3-14 NHCOBu-i 4-Me —3-15 NHCOBu-s 4-Me — 3-16 NHCOBu-t 4-Me — 3-17 NHCOBu-t 4-OMe — 3-18NHCOCH₂CF₃ 4-Me — 3-19 NHCOC₂F₅ 4-Me — 3-20 NHCOCH₂CH₂F 4-Me — 3-21NHCOC(CH₃)₂CF₃ 4-Me — 3-22 NHCOCH₂CH₂CF₃ 4-Me — 3-23 NHCOCH₂C₂F₅ 4-Me —3-24 NHCOCH₂CH═CH₂ 4-Me — 3-25 NHCOCH₂CH═CMe₂ 4-Me — 3-26NHCOC(CH₃)₂CH═CH₂ 4-Me — 3-27 NHCOC(CH₃)₂CH═CHCH₃ 4-Me — 3-28NHCOCH₂CH═CHCl 4-Me — 3-29 NHCOCH₂CH═CHCF₃ 4-Me — 3-30 NHCOCH₂CI═CI₂4-Me — 3-31 NHCO(1,1-dimethyl-2- 4-Me — propynyl) 3-32 NHCO(2-butynyl)4-Me — 3-33 NHCO(1,1-dimethyl-2- 4-Me — butynyl) 3-34NHCO(1,1-dimethyl-2- 4-Me — pentynyl) 3-35 NHCO(1-propynyl) 4-Me — 3-36NHCO(1,1-dimethyl-3-Iodo- 4-Me — 2-pentynyl) 3-37NHCO(4,4,4-trifluoro-2- 4-Me — butynyl) 3-38 NHCOPr-c 4-Me — 3-39NHCOHex-c 4-Me — 3-40 NHCO(CH₂)₄CO₂H 4-Me — 3-41 NHCOCH₂CH₂NHCO₂Bu-t4-Me — 3-42 NHCOCH₂CH₂NHCO₂Et 4-Me — 3-43 NHCOCH₂CH₂CH₂NHCOCH₃ 4-Me —3-44 NHCOCH₂CH₂CH₂NHMe₂ 4-Me — 3-45 NHCOCH₂CH₂N(Me)COCH₃ 4-Me — 3-46NHCOCH₂CH₂NHCOPh 4-Me — 3-47 NHCOCH₂CH₂N(Me)COPh 4-Me — 3-48NHCOCH₂CH₂NHPh 4-Me — 3-49 NHCO(CH₂)₄NH₂ 4-Me — 3-50 NHCOCH₂NHCH₂Ph 4-Me— 3-51 NHCOCH₂N(CH₂Ph)(CO₂Bu-t) 4-Me — 3-52 NHCOCH₂CH₂OC₆H₄Cl-4 4-Me —3-53 NHCOCH₂OPh 4-Me — 3-54 NHCOCH₂OC₆H₄F-3 4-Me — 3-55NHCOCH₂OC₆H₄OCF₃-3 4-Me — 3-56 NHCO(CH₂)₄SMe 4-Me — 3-57 NHCOCH₂CH₂OEt4-Me — 3-58 NHCOCH₂CH₂OPr-i 4-Me — 3-59 NHCOCH₂CH₂OBu-i 4-Me — 3-60NHCOCH₂CH₂OCH₂CH₂OMe 4-Me — 3-61 NHCO₂CH₃ 4-Me — 3-62 NHCO₂C₂H₅ 4-Me —3-63 NHCO₂Pr-n 4-Me — 3-64 NHCO₂Pr-i 4-Me — 3-65 NHCO₂Bu-n 4-Me — 3-66NHCO₂Bu-i 4-Me — 3-67 NHCO₂Bu-s 4-Me — 3-68 NHCO₂Bu-t 4-i-Pr — 3-69NHCO₂Bu-t 5-Me — 3-70 NHCO₂Bu-t 4-t-Bu — 3-71 NHCO₂Bu-t 4-Me — 3-72NHCO₂Bu-t 4-Et — 3-73 NHCO₂Bu-t 4-CH═CH2 — 3-74 NHCO₂Bu-t 4-OMe — 3-75NHCO₂Bu-t 4-OEt — 3-76 NHCO₂Bu-t 4-OCH₂CH₂OEt — 3-77 NHCO₂Bu-t 4-OPr-i —3-78 NHCO₂Bu-t 4-OBu-n — 3-79 NHCO₂Bu-t 4-SMe — 3-80 NHCO₂Bu-t 4-SOMe —3-81 NHCO₂Bu-t 4-SO₂Me — 3-82 NHCO₂Bu-t 4-NMe₂ — 3-83 NHCO₂Bu-t4-N(Me)(CO₂Bu-t) — 3-84 NHCO₂Bu-t 5-CN — 3-85 NHCO₂Bu-t 4-CN — 3-86NHCO₂Bu-t 4-morphorino — 3-87 NHCO₂Bu-t 5-Ph — 3-88 NHCO₂Bu-t 5-CO₂C₂H₅— 3-89 NHCO₂Bu-t 5-CONHCH₃ — 3-90 NHCO₂Bu-t CF₃ — 3-91 NHCO₂Bu-t 5-OH —3-92 NHCO₂Bu-t 5-SH — 3-93 NHCO₂Bu-t 4-CH₂CI═CI₂ — 3-94 NHCO₂Bu-t4-etynyl — 3-95 NHCO₂Bu-t 4-propargyl — 3-96 NHCO₂Bu-t 4-(3-iodo-2- —propynyl) 3-97 NHCO₂Bu-t 4-Ph — 3-98 NHCO₂Bu-t 4-C₆H₄OMe-4 — 3-99NHCO₂Bu-t 4-(2-pyridyl) — 3-100 NHCO₂Bu-t 4-(4-CF₃-2- — oxazolyl) 3-101NHCO₂Bu-t 4-(3-CF₃-5-Cl-2- — pyridyl) 3-102 NHCO₂Bu-t 4-pyrrolidino —3-103 NHCO₂Bu-t 4-COMe — 3-104 NHCO₂Bu-t 4-CONHMe — 3-105 NHCO₂Bu-t4-CONMe₂ — 3-106 NHCO₂Bu-t 4-COPr-c — 3-107 NHCO₂Bu-t 4-COPh — 3-108NHCO₂Bu-t 4-COCH₂CH═CH₂ — 3-109 NHCO₂Bu-t 4-CO(propargyl) — 3-110NHCO₂Bu-t 4-CO₂Me — 3-111 NHCO₂Bu-t 4-CO₂Ph — 3-112 NHCO₂Bu-t4-CO₂CH₂CH═CH₂ — 3-113 NHCO₂Bu-t 4-CO₂(propargyl) — 3-114 NHCO₂Bu-t 4-Me2-Cl 3-115 NHCO₂Bu-t 4-Me 3-Cl 3-116 NHCO₂Bu-t 4-Me 4-Cl 3-117 NHCO₂Bu-t4-Me 2,4-Cl₂ 3-118 NHCO₂Bu-t 4-Me 3,5-Cl₂ 3-119 NHCO₂Bu-t 4-Me 3,4,5-Cl₃ 3-120 NHCO₂Bu-t 4-Me 2-Me 3-121 NHCO₂Bu-t 3,4-diMe — 3-122 NHCO₂Bu-t3,5-diMe — 3-123 NHCO₂Bu-t 4,5-diMe — 3-124 NHCO₂Bu-t 3,4,5-triMe —3-125 NHCO₂Bu-t 3-Cl-4-Me — 3-126 NHCO₂Bu-t 5-Cl-4-Me — 3-127 NHCO₂Bu-t3,5-diCl-4-Me — 3-128 NHCO₂Bu-t 3,5-diCl — 3-129 NHCO₂Bu-t 3,4-diCl —3-130 NHCO₂Bu-t 3,4-diF — 3-131 NHCO₂Bu-n 4-NH₂ — 3-132 NHCO₂Bu-n4-NHCO₂Bu-t — 3-133 NHCO₂CH₂CF₃ 4-Me — 3-134 NHCO₂C₂F₅ 4-Me — 3-135NHCO₂CH₂CH₂F 4-Me — 3-136 NHCO₂C(CH₃)₂CF₃ 4-Me — 3-137 NHCO₂CH₂CH₂CF₃4-Me — 3-138 NHCO₂CH₂C₂F₅ 4-Me — 3-139 NHCO₂CH₂CH═CH₂ 4-Me — 3-140NHCO₂CH₂CH═CMe₂ 4-Me — 3-141 NHCO₂C(CH₃)₂CH═CH₂ 4-Me — 3-142NHCO₂C(CH₃)₂CH═CHCH₃ 4-Me — 3-143 NHCO₂CH₂CH═CHCl 4-Me — 3-144NHCO₂CH₂CH═CHCF₃ 4-Me — 3-145 NHCO₂CH₂CI═CI₂ 4-Me — 3-146NHCO₂(1,1-dimethyl-2- 4-Me — propynyl) 3-147 NHCO₂(2-butynyl) 4-Me —3-148 NHCO₂(1,1-dimethyl-2- 4-Me — butynyl) 3-149 NHCO₂(1,1-dimethyl-2-4-Me — pentynyl) 3-150 NHCO₂(1-propynyl) 4-Me — 3-151NHCO₂(1,1-dimethyl-3-Iodo- 4-Me — 2-pentynyl) 3-152NHCO₂(4,4,4-trifluoro-2- 4-Me — butynyl) 3-153 NHCO₂Pr-c 4-Me — 3-154NHCO₂Hex-c 4-Me — 3-155 NHCO₂CH₂CH₂NHCO₂Bu-t 4-Me — 3-156NHCO₂CH₂CH₂NHCO₂Et 4-Me — 3-157 NHCO₂CH₂CH₂CH₂NHCOCH₃ 4-Me — 3-158NHCO₂CH₂CH₂CH₂NHMe₂ 4-Me — 3-159 NHCO₂CH₂CH₂N(Me)COCH₃ 4-Me — 3-160NHCO₂CH₂CH₂NHCOPh 4-Me — 3-161 NHCO₂CH₂CH₂N(Me)COPh 4-Me — 3-162NHCO₂CH₂CH₂NHPh 4-Me — 3-163 NHCO₂(CH₂)₄NH₂ 4-Me — 3-164 NHCO₂CH₂NHCH₂Ph4-Me — 3-165 NHCO₂CH₂N(CH₂Ph)(CO₂Bu-t) 4-Me — 3-166 NHCO₂CH₂C₃H₅-c 4-Me— 3-167 NHCO₂CH(CH₃)C₃H₅-c 4-Me — 3-168 NHCO₂CH₂C₆H₁₁-c 4-Me — 3-169NHCO₂CH₂Ph 4-Me — 3-170 NHCO₂CH(CH₃)CH₂Ph 4-Me — 3-171 NHCO₂CH(CH₃)Ph4-Me — 3-172 NHCO₂C(CH₃)₂Ph 4-Me — 3-173 NHCO₂CH₂C₆H₄CF₃-4 4-Me — 3-174NHCO₂CH₂C₆H₄CN-4 4-Me — 3-175 NHCO₂CH₂C₆H₄CN-3 4-Me — 3-176NHCO₂CH₂C₆H₄Cl-4 4-Me — 3-177 NHCO₂CH₂C₆H₄Cl-3 4-Me — 3-178NHCO₂CH₂C₆H₄OMe-3 4-Me — 3-179 NHCO₂CH₂C₆H₄OMe-2 4-Me — 3-180NHCO₂CH₂C₆H₄Me-4 4-Me — 3-181 NHCO₂CH₂C₆H₄Me-3 4-Me — 3-182NHCO₂CH₂C₆H₄Me-2 4-Me — 3-183 NHCO₂CH₂C₆H₄SO₂Me-4 4-Me — 3-184NHCO₂CH₂C₆H₄SO₂Me-3 4-Me — 3-185 NHCO₂CH₂C₆H₄Ph-4 4-Me — 3-186NHCO₂CH₂C₆H₄Ph-3 4-Me — 3-187 NHCO₂CH₂Py-2 4-Me — 3-188NHCO₂CH₂(6-Me-2-Py) 4-Me — 3-189 NHCO₂C(CH₃)₂Py-4 4-Me — 3-190NHCO₂CH₂(2-thiazolyl) 4-Me — 3-191 NHCO₂CH₂(2-benzthiazolyl) 4-Me —3-192 NHCO₂CH₂CH₂OMe 4-Me — 3-193 NHCO₂CH₂CH₂OEt 4-Me — 3-194NHCO₂CH₂CH₂OPr-i 4-Me — 3-195 NHCO₂CH₂CH₂OBu-i 4-Me — 3-196NHCO₂CH₂CH₂OCH₂CH₂OMe 4-Me — 3-197 NHCO₂CH₂CH₂OEt 4-i-Pr — 3-198NHCO₂CH₂CH₂OC₆H₄Cl-4 4-Me — 3-199 NHCOCH₂OPh 4-Me — 3-200NHCOCH₂OC₆H₄F-3 4-Me — 3-201 NHCOCH₂OC₆H₄OCF₃-3 4-Me — 3-202NHCO₂CH₂CH₂OCH₂Ph 4-Me — 3-203 NHCO₂CH₂CH₂OCH₂CH₂Ph 4-Me — 3-204NHCO₂(1,1-dimethyl-3- 4-Me — phenyl-2-pentynyl) 3-205 NHCO₂(CH₂)₄SMe4-Me — 3-206 NHCO₂(CH₂)₄SCF₃ 4-Me — 3-207 NHCO₂(CH₂)₄SPh 4-Me — 3-208NHCO₂(CH₂)₄SOMe 4-Me — 3-209 NHCO₂(CH₂)₄SOCF₃ 4-Me — 3-210NHCO₂(CH₂)₄SOPh 4-Me — 3-211 NHCO₂(CH₂)₄SO₂Me 4-Me — 3-212NHCO₂(CH₂)₄SO₂CF₃ 4-Me — 3-213 NHCO₂(CH₂)₄SO₂Ph 4-Me — 3-214 NHCO₂Ph4-Me — 3-215 NHCO₂C₆H₄OMe-4 4-Me — 3-216 NHCONHMe 4-Me — 3-217NHCONHC₂H₅ 4-Me — 3-218 NHCONHPr-n 4-Me — 3-219 NHCONHBu-t 4-Me — 3-220NHCONHBu-s 4-Me — 3-221 NHCONH(Hex-n) 4-Me — 3-222 H 4-Cl — 3-223 NH₂4-Cl — 3-224 NHCHO 4-Cl — 3-225 NHCOCH₂CF₃ 4-Cl — 3-226 NHCOC₂F₅ 4-Cl —3-227 NHCOCH₂CH₂F 4-Cl — 3-228 NHCOC(CH₃)₂CF₃ 4-Cl — 3-229 NHCOCH₂CH₂CF₃4-Cl — 3-230 NHCOCH₂C₂F₅ 4-Cl — 3-231 NHCOCH₂CH═CH₂ 4-Cl — 3-232NHCOCH₂CH═CMe₂ 4-Cl — 3-233 NHCOC(CH₃)₂CH═CH₂ 4-Cl — 3-234NHCOC(CH₃)₂CH═CHCH₃ 4-Cl — 3-235 NHCOCH₂CH═CHCl 4-Cl — 3-236NHCOCH₂CH═CHCF₃ 4-Cl — 3-237 NHCOCH₂CI═CI₂ 4-Cl — 3-238NHCO(1,1-dimethyl-2- 4-Cl — propynyl) 3-239 NHCO(2-butynyl) 4-Cl — 3-240NHCO(1,1-dimethyl-2- 4-Cl — butynyl) 3-241 NHCO(1,1-dimethyl-2- 4-Cl —pentynyl) 3-242 NHCO(1-propynyl) 4-Cl — 3-243 NHCO(1,1-dimethyl-3-Iodo-4-Cl — 2-pentynyl) 3-244 NHCO(4,4,4-trifluoro-2- 4-Cl — butynyl) 3-245NHCOPr-c 4-Cl — 3-246 NHCOHex-c 4-Cl — 3-247 NHCO(CH₂)₄CO₂H 4-Cl — 3-248NHCOCH₂CH₂NHCO₂Bu-t 4-Cl — 3-249 NHCOCH₂CH₂NHCO₂Et 4-Cl — 3-250NHCOCH₂CH₂CH₂NHCOCH₃ 4-Cl — 3-251 NHCOCH₂CH₂CH₂NHMe₂ 4-Cl — 3-252NHCOCH₂CH₂N(Me)COCH₃ 4-Cl — 3-253 NHCOCH₂CH₂NHCOPh 4-Cl — 3-254NHCOCH₂CH₂N(Me)COPh 4-Cl — 3-255 NHCOCH₂CH₂NHPh 4-Cl — 3-256NHCO(CH₂)₄NH₂ 4-Cl — 3-257 NHCOCH₂NHCH₂Ph 4-Cl — 3-258NHCOCH₂N(CH₂Ph)(CO₂Bu-t) 4-Cl — 3-259 NHCOCH₂CH₂OC₆H₄Cl-4 4-Cl — 3-260NHCOCH₂OPh 4-Cl — 3-261 NHCOCH₂OC₆H₄F-3 4-Cl — 3-262 NHCOCH₂OC₆H₄OCF₃-34-Cl — 3-263 NHCO(CH₂)₄SMe 4-Cl — 3-264 NHCOCH₂CH₂OEt 4-Cl — 3-265NHCOCH₂CH₂OPr-i 4-Cl — 3-266 NHCOCH₂CH₂OBu-i 4-Cl — 3-267NHCOCH₂CH₂OCH₂CH₂OMe 4-Cl — 3-268 NHCO₂CH₃ 4-Cl — 3-269 NHCO₂C₂H₅ 4-Cl —3-270 NHCO₂Pr-n 4-Cl — 3-271 NHCO₂Pr-i 4-Cl — 3-272 NHCO₂Bu-n 4-Cl —3-273 NHCO₂Bu-i 4-Cl — 3-274 NHCO₂Bu-s 4-Cl — 3-275 NHCO₂Bu-t 4-Cl —3-276 NHCO₂Bu-t 5-Br — 3-277 NHCO₂Bu-t 5-Cl — 3-278 NHCO₂Bu-t 4-Br —3-279 NHCO₂Bu-t 4-Cl 2-Cl 3-280 NHCO₂Bu-t 4-Cl 3-Cl 3-281 NHCO₂Bu-t 4-Cl4-Cl 3-282 NHCO₂Bu-t 4-Cl 2,4-Cl₂ 3-283 NHCO₂Bu-t 4-Cl 3,5-Cl₂ 3-284NHCO₂Bu-t 4-Cl 3,4,5- Cl₃ 3-285 NHCO₂Bu-t 4-Cl 2-Me 3-286 NHCO₂CH₂CF₃4-Cl — 3-287 NHCO₂C₂F₅ 4-Cl — 3-288 NHCO₂CH₂CH₂F 4-Cl — 3-289NHCO₂C(CH₃)₂CF₃ 4-Cl — 3-290 NHCO₂CH₂CH₂CF₃ 4-Cl — 3-291 NHCO₂CH₂C₂F₅4-Cl — 3-292 NHCO₂CH₂CH═CH₂ 4-Cl — 3-293 NHCO₂CH₂CH═CMe₂ 4-Cl — 3-294NHCO₂C(CH₃)₂CH═CH₂ 4-Cl — 3-295 NHCO₂C(CH₃)₂CH═CHCH₃ 4-Cl — 3-296NHCO₂CH₂CH═CHCl 4-Cl — 3-297 NHCO₂CH₂CH═CHCF₃ 4-Cl — 3-298NHCO₂CH₂CI═CI₂ 4-Cl — 3-299 NHCO₂(1,1-dimethyl-2- 4-Cl — propynyl) 3-300NHCO₂(2-butynyl) 4-Cl — 3-301 NHCO₂(1,1-dimethyl-2- 4-Cl — butynyl)3-302 NHCO₂(1,1-dimethyl-2- 4-Cl — pentynyl) 3-303 NHCO₂(1-propynyl)4-Cl — 3-304 NHCO₂(1,1-dimethyl-3-Iodo- 4-Cl — 2-pentynyl) 3-305NHCO₂(4,4,4-trifluoro-2- 4-Cl — butynyl) 3-306 NHCO₂Pr-c 4-Cl — 3-307NHCO₂Hex-c 4-Cl — 3-308 NHCO₂CH₂CH₂NHCO₂Bu-t 4-Cl — 3-309NHCO₂CH₂CH₂NHCO₂Et 4-Cl — 3-310 NHCO₂CH₂CH₂CH₂NHCOCH₃ 4-Cl — 3-311NHCO₂CH₂CH₂CH₂NMe₂ 4-Cl — 3-312 NHCO₂CH₂CH₂N(Me)COCH₃ 4-Cl — 3-313NHCO₂CH₂CH₂NHCOPh 4-Cl — 3-314 NHCO₂CH₂CH₂N(Me)COPh 4-Cl — 3-315NHCO₂CH₂CH₂NHPh 4-Cl — 3-316 NHCO₂(CH₂)₄NH₂ 4-Cl — 3-317 NHCO₂CH₂NHCH₂Ph4-Cl — 3-318 NHCO₂CH₂N(CH₂Ph)(CO₂Bu-t) 4-Cl — 3-319 NHCO₂CH₂C₃H₅-c 4-Cl— 3-320 NHCO₂CH(CH₃)C₃H₅-c 4-Cl — 3-321 NHCO₂CH₂C₆H₁₁-c 4-Cl — 3-322NHCO₂CH₂Ph 4-Cl — 3-323 NHCO₂CH₂Ph 5-Cl — 3-324 NHCO₂CH(CH₃)CH₂Ph 4-Cl —3-325 NHCO₂CH(CH₃)Ph 4-Cl — 3-326 NHCO₂C(CH₃)₂Ph 4-Cl — 3-327NHCO₂CH₂C₆H₄CF₃-4 4-Cl — 3-328 NHCO₂CH₂C₆H₄CN-4 4-Cl — 3-329NHCO₂CH₂C₆H₄CN-3 4-Cl — 3-330 NHCO₂CH₂C₆H₄Cl-4 4-Cl — 3-331NHCO₂CH₂C₆H₄Cl-3 4-Cl — 3-332 NHCO₂CH₂C₆H₄OMe-3 4-Cl — 3-333NHCO₂CH₂C₆H₄OMe-2 4-Cl — 3-334 NHCO₂CH₂C₆H₄Me-4 4-Cl — 3-335NHCO₂CH₂C₆H₄Me-3 4-Cl — 3-336 NHCO₂CH₂C₆H₄Me-2 4-Cl — 3-337NHCO₂CH₂C₆H₄SO₂Me-4 4-Cl — 3-338 NHCO₂CH₂C₆H₄SO₂Me-3 4-Cl — 3-339NHCO₂CH₂C₆H₄Ph-4 4-Cl — 3-340 NHCO₂CH₂C₆H₄Ph-3 4-Cl — 3-341 NHCO₂CH₂Py-24-Cl — 3-342 NHCO₂CH₂(6-Me-2-Py) 4-Cl — 3-343 NHCO₂C(CH₃)₂Py-4 4-Cl —3-344 NHCO₂CH₂(2-thiazolyl) 4-Cl — 3-345 NHCO₂CH₂(2-benzthiazolyl) 4-Cl— 3-346 NHCO₂CH₂CH₂OMe 4-Cl — 3-347 NHCO₂CH₂CH₂OEt 4-Cl — 3-348NHCO₂CH₂CH₂OPr-i 4-Cl — 3-349 NHCO₂CH₂CH₂OBu-i 4-Cl — 3-350NHCO₂CH₂CH₂OCH₂CH₂OMe 4-Cl — 3-351 NHCO₂CH₂CH₂OC₆H₄Cl-4 4-Cl — 3-352NHCOCH₂OPh 4-Cl — 3-353 NHCOCH₂OC₆H₄F-3 4-Cl — 3-354 NHCOCH₂OC₆H₄OCF₃-34-Cl — 3-355 NHCO₂CH₂CH₂OCH₂Ph 4-Cl — 3-356 NHCO₂(1,1-dimethyl-3- 4-Cl —phenyl-2-pentynyl) 3-357 NHCO₂CH₂CH₂OCH₂CH₂Ph 4-Cl — 3-358NHCO₂(1,1-dimethyl-3- 4-Cl — phenyl-2-pentynyl) 3-359 NHCO₂(CH₂)₄SMe4-Cl — 3-360 NHCO₂(CH₂)₄SCF₃ 4-Cl — 3-361 NHCO₂(CH₂)₄SPh 4-Cl — 3-362NHCO₂(CH₂)₄SOMe 4-Cl — 3-363 NHCO₂(CH₂)₄SOCF₃ 4-Cl — 3-364NHCO₂(CH₂)₄SOPh 4-Cl — 3-365 NHCO₂(CH₂)₄SO₂Me 4-Cl — 3-366NHCO₂(CH₂)₄SO₂CF₃ 4-Cl — 3-367 NHCO₂(CH₂)₄SO₂Ph 4-Cl — 3-368 NHCO₂Ph4-Cl — 3-369 NHCO₂C₆H₄OMe-4 4-Cl — 3-370 NHCONHMe 4-Cl — 3-371NHCONHC₂H₅ 4-Cl — 3-372 NHCONHPr-n 4-Cl — 3-373 NHCONHBu-t 4-Cl — 3-374NHCONHBu-s 4-Cl — 3-375 NHCONH(Hex-n) 4-Cl — 3-376 NHCOCH₂CF₃ — — 3-377NHCOC₂F₅ — — 3-378 NHCOCH₂CH₂F — — 3-379 NHCOC(CH₃)₂CF₃ — — 3-380NHCOCH₂CH₂CF₃ — — 3-381 NHCOCH₂C₂F₅ — — 3-382 NHCOCH₂CH═CH₂ — — 3-383NHCOCH₂CH═CMe₂ — — 3-384 NHCOC(CH₃)₂CH═CH₂ — — 3-385 NHCOC(CH₃)₂CH═CHCH₃— — 3-386 NHCOCH₂CH═CHCl — — 3-387 NHCOCH₂CH═CHCF₃ — — 3-388NHCOCH₂CI═CI₂ — — 3-389 NHCO(1,1-dimethyl-2- — — propynyl) 3-390NHCO(2-butynyl) — — 3-391 NHCO(1,1-dimethyl-2- — — butynyl) 3-392NHCO(1,1-dimethyl-2- — — pentynyl) 3-393 NHCO(1-propynyl) — — 3-394NHCO(1,1-dimethyl-3-Iodo- — — 2-pentynyl) 3-395 NHCO(4,4,4-trifluoro-2-— — butynyl) 3-396 NHCO(CH₂)₄CO₂H — — 3-397 NHCOCH₂CH₂CH₂NHMe₂ — — 3-398NHCO(CH₂)₄NH₂ — — 3-399 NHCOCH₂NHCH₂Ph — — 3-400NHCOCH₂N(CH₂Ph)(CO₂Bu-t) — — 3-401 NHCOCH₂CH₂NMe₂ — — 3-402NHCOCH₂CH₂NHEt — — 3-403 NHCOCH₂CH₂NHPr-n — — 3-404 NHCOCH₂CH₂OC₆H₄Cl-4— — 3-405 NHCOCH₂OPh — — 3-406 NHCOCH₂OC₆H₄F-3 — — 3-407NHCOCH₂OC₆H₄OCF₃-3 — — 3-408 NHCOCH₂OC₆H₄CN-2 — — 3-409 NHCOCH₂OC₆H₄F-4— — 3-410 NHCOCH₂OC₆H₃(3,4- — — methylenedioxy) 3-411NHCOCH₂OC₆H₄(CONH₂)-2 — — 3-412 NHCOCH₂OC₆H₃(3,4-(OCH₃)₂) — — 3-413NHCOCH₂O(6-CF₃-pyrimidin- — — 4-yl) 3-414 NHCOCH₂O(3-Py) — — 3-415NHCO₂CH₂CF₃ — — 3-416 NHCO₂C₂F₅ — — 3-417 NHCO₂CH₂CH₂F — — 3-418NHCO₂C(CH₃)₂CF₃ — — 3-419 NHCO₂CH₂CH₂CF₃ — — 3-420 NHCO₂CH₂C₂F₅ — —3-421 NHCO₂CH₂CH═CH₂ — — 3-422 NHCO₂CH₂CH═CMe₂ — — 3-423NHCO₂C(CH₃)₂CH═CH₂ — — 3-424 NHCO₂C(CH₃)₂CH═CHCH₃ — — 3-425NHCO₂CH₂CH═CHCl — — 3-426 NHCO₂CH₂CH═CHCF₃ — — 3-427 NHCO₂CH₂CI═CI₂ — —3-428 NHCO₂(1,1-dimethyl-2- — — propynyl) 3-429 NHCO₂(2-butynyl) — —3-430 NHCO₂(1,1-dimethyl-2- — — butynyl) 3-431 NHCO₂(1,1-dimethyl-2- — —pentynyl) 3-432 NHCO₂(1-propynyl) — — 3-433 NHCO₂(1,1-dimethyl-3-Iodo- —— 2-pentynyl) 3-434 NHCO₂(4,4,4-trifluoro-2- — — butynyl) 3-435NHCO₂(1,1-dimethyl-3- — — phenyl-2-pentynyl) 3-436 NHCO₂CH₂CH₂NHCO₂Bu-t— — 3-437 NHCO₂CH₂CH₂NHCO₂Et — — 3-438 NHCO₂CH₂N(CH₂Ph)(CO₂Bu-t) — —3-439 NHCO₂CH₂NCH₂Ph — — 3-440 NHCO₂CH₂CH₂NCH₂Ph — — 3-441NHCO₂CH₂CH₂NCH₂C₆H₄Cl-4 — — 3-442 NHCO₂CH₂CH₂NHMe — — 3-443NHCO₂CH₂C(CH₃)₂N(CH₃)₂ — — 3-444 NHCO₂CH(CH₃)CH₂N(CH₃)₂ — — 3-445NHCO₂CH₂C₃H₅-c — — 3-446 NHCO₂CH(CH₃)C₃H₅-c — — 3-447 NHCO₂CH₂C₆H₁₁-c —— 3-448 NHCO₂CH(CH₃)CH₂Ph — — 3-449 NHCO₂CH(CH₃)Ph — — 3-450NHCO₂C(CH₃)₂Ph — — 3-451 NHCO₂CH₂C₆H₄CF₃-4 — — 3-452 NHCO₂CH₂C₆H₄CN-4 —— 3-453 NHCO₂CH₂C₆H₄CN-3 — — 3-454 NHCO₂CH₂C₆H₄Cl-4 — — 3-455NHCO₂CH₂C₆H₄Cl-3 — — 3-456 NHCO₂CH₂C₆H₄OMe-3 — — 3-457 NHCO₂CH₂C₆H₄OMe-2— — 3-458 NHCO₂CH₂C₆H₄Me-4 — — 3-459 NHCO₂CH₂C₆H₄Me-3 — — 3-460NHCO₂CH₂C₆H₄Me-2 — — 3-461 NHCO₂CH₂C₆H₄SO₂Me-4 — — 3-462NHCO₂CH₂C₆H₄SO₂Me-3 — — 3-463 NHCO₂CH₂C₆H₄Ph-4 — — 3-464NHCO₂CH₂C₆H₄Ph-3 — — 3-465 NHCO₂CH₂C₆H₄OCH₃-4 — — 3-466NHCO₂CH₂C₆H₃(3,4- methylenedioxy) 3-467 NHCO₂CH₂Py-2 — — 3-468NHCO₂CH₂(6-Me-2-Py) — — 3-469 NHCO₂C(CH₃)₂Py-4 — — 3-470NHCO₂CH₂(2-thiazolyl) — — 3-471 NHCO₂CH₂(2-benzthiazolyl) — — 3-472NHCO₂CH₂(3-Py) — — 3-473 NHCO₂CH₂(4-Py) — — 3-474 NHCO₂CH(CH₃)(4-Py) — —3-475 NHCO₂CH₂CH₂OMe — — 3-476 NHCO₂CH₂CH₂OEt — — 3-477 NHCO₂CH₂CH₂OPr-i— — 3-478 NHCO₂CH₂CH₂OBu-i — — 3-479 NHCO₂CH₂CH₂OCH₂CH₂OMe — — 3-480NHCO₂C(CH₃)₂CH₂OCH₃ — — 3-481 NHCO₂CH(CH₃)CH₂OCH₃ — — 3-482NHCO₂CH₂CH₂OC₆H₄Cl-4 — — 3-483 NHCO₂CH₂OPh — — 3-484 NHCO₂CH₂OC₆H₄F-3 —— 3-485 NHCO₂CH₂OC₆H₄OCF₃-3 — — 3-486 NHCO₂CH₂CH₂OCH₂Ph — — 3-487NHCO₂CH₂CH₂OCH₂CH₂Ph — — 3-488 NHCO₂(CH₂)₄SMe — — 3-489 NHCO₂(CH₂)₄SCF₃— — 3-490 NHCO₂(CH₂)₄SPh — — 3-491 NHCO₂(CH₂)₄SOMe — — 3-492NHCO₂(CH₂)₄SOCF₃ — — 3-493 NHCO₂(CH₂)₄SOPh — — 3-494 NHCO₂(CH₂)₄SO₂Me —— 3-495 NHCO₂(CH₂)₄SO₂CF₃ — — 3-496 NHCO₂(CH₂)₄SO₂Ph — — 3-497 NHCO₂Ph —— 3-498 NHCO₂C₆H₄OMe-4 — — 3-499 NHCOCH₂CH₂CH₂COCH₃ — —

TABLE 4

mp No Z¹¹ R¹¹ (X )_(n 1) ° C. 4-1 H Me — 4-2 NH₂ Me — 4-3 NH₂ Bu-t — 4-4NH₂ OC₂H₅ — 4-5 NH₂ OCH₃ — 4-6 NH₂ C₂H₅ — 4-7 NHCHO Me — 4-8 NHCOCH₃ Me— 4-9 NHCOC₂H₅ Me — 4-10 NHCOPr-n Me — 4-11 NHCOPr-i Me — 4-12 NHCOBu-nMe — 4-13 NHCOBu-i Me — 4-14 NHCOBu-s Me — 4-15 NHCOBu-t Me — 4-16NHCOBu-t OMe — 4-17 NHCOCH₂CF₃ Me — 4-18 NHCOC₂F₅ Me — 4-19 NHCOCH₂CH₂FMe — 4-20 NHCOC(CH₃)₂CF₃ Me — 4-21 NHCOCH₂CH₂CF₃ Me — 4-22 NHCOCH₂C₂F₅Me — 4-23 NHCOCH₂CH═CH₂ Me — 4-24 NHCOCH₂CH═CMe₂ Me — 4-25NHCOC(CH₃)₂CH═CH₂ Me — 4-26 NHCOC(CH₃)₂CH═CHCH₃ Me — 4-27 NHCOCH₂CH═CHClMe — 4-28 NHCOCH₂CH═CHCF₃ Me — 4-29 NHCOCH₂CI═CI₂ Me — 4-30NHCO(1,1-dimethyl-2- Me — propynyl) 4-31 NHCO(2-butynyl) Me — 4-32NHCO(1,1-dimethyl-2- Me — butynyl) 4-33 NHCO(1,1-dimethyl-2- Me —pentynyl) 4-34 NHCO(1-propynyl) Me — 4-35 NHCO(1,1-dimethyl-3-Iodo- Me —2-pentynyl) 4-36 NHCO(4,4,4-trifluoro-2- Me — butynyl) 4-37 NHCOPr-c Me— 4-38 NHCOHex-c Me — 4-39 NHCO(CH₂)₄CO₂H Me — 4-40 NHCOCH₂CH₂NHCO₂Bu-tMe — 4-41 NHCOCH₂CH₂NHCO₂Et Me — 4-42 NHCOCH₂CH₂CH₂NHCOCH₃ Me — 4-43NHCOCH₂CH₂CH₂NHMe₂ Me — 4-44 NHCOCH₂CH₂N(Me)COCH₃ Me — 4-45NHCOCH₂CH₂NHCOPh Me — 4-46 NHCOCH₂CH₂N(Me)COPh Me — 4-47 NHCOCH₂CH₂NHPhMe — 4-48 NHCO(CH₂)₄NH₂ Me — 4-49 NHCOCH₂NHCH₂Ph Me — 4-50NHCOCH₂N(CH₂Ph) Me — (CO₂Bu-t) 4-51 NHCOCH₂CH₂OC₆H₄Cl-4 Me — 4-52NHCOCH₂OPh Me — 4-53 NHCOCH₂OC₆H₄F-3 Me — 4-54 NHCOCH₂OC₆H₄OCF₃-3 Me —4-55 NHCO(CH₂)₄SMe Me — 4-56 NHCOCH₂CH₂OEt Me — 4-57 NHCOCH₂CH₂OPr-i Me— 4-58 NHCOCH₂CH₂OBu-i Me — 4-59 NHCOCH₂CH₂OCH₂CH₂OMe Me — 4-60 NHCO₂CH₃Me — 4-61 NHCO₂C₂H₅ Me — 4-62 NHCO₂Pr-n Me — 4-63 NHCO₂Pr-i Me — 4-64NHCO₂Bu-n Me — 4-65 NHCO₂Bu-i Me — 4-66 NHCO₂Bu-s Me — 4-67 NHCO₂Bu-ti-Pr — 4-68 NHCO₂Bu-t Me — 4-69 NHCO₂Bu-t t-Bu — 4-70 NHCO₂Bu-t Et —4-71 NHCO₂Bu-t CH═CH₂ — 4-72 NHCO₂Bu-t OMe — 4-73 NHCO₂Bu-t OEt — 4-74NHCO₂Bu-t OCH₂CH₂OEt — 4-75 NHCO₂Bu-t OPr-i — 4-76 NHCO₂Bu-t OBu-n —4-77 NHCO₂Bu-t SMe — 4-78 NHCO₂Bu-t SOMe — 4-79 NHCO₂Bu-t SO₂Me — 4-80NHCO₂Bu-t NMe₂ — 4-81 NHCO₂Bu-t N(Me) — (CO₂Bu-t) 4-82 NHCO₂Bu-t CN —4-83 NHCO₂Bu-t morphorino — 4-84 NHCO₂Bu-t Ph — 4-85 NHCO₂Bu-t CO₂C₂H₅ —4-86 NHCO₂Bu-t CONHCH₃ — 4-87 NHCO₂Bu-t CF₃ — 4-88 NHCO₂Bu-t OH — 4-89NHCO₂Bu-t SH — 4-90 NHCO₂Bu-t CH₂CI═CI₂ — 4-91 NHCO₂Bu-t etynyl — 4-92NHCO₂Bu-t propargyl — 4-93 NHCO₂Bu-t (3-iodo-2- — propynyl) 4-94NHCO₂Bu-t Ph — 4-95 NHCO₂Bu-t C₆H₄OMe-4 — 4-96 NHCO₂Bu-t 2-pyridyl —4-97 NHCO₂Bu-t 4-CF₃-2- — oxazolyl 4-98 NHCO₂Bu-t 3-CF₃-5-Cl-2- —pyridyl 4-99 NHCO₂Bu-t pyrrolidino — 4-100 NHCO₂Bu-t COMe — 4-101NHCO₂Bu-t CONHMe — 4-102 NHCO₂Bu-t CONMe₂ — 4-103 NHCO₂Bu-t COPr-c —4-104 NHCO₂Bu-t COPh — 4-105 NHCO₂Bu-t COCH₂CH═CH₂ — 4-106 NHCO₂Bu-tCO(propargyl) — 4-107 NHCO₂Bu-t CO₂Me — 4-108 NHCO₂Bu-t CO₂Ph — 4-109NHCO₂Bu-t CO₂CH₂CH═CH₂ — 4-110 NHCO₂Bu-t CO₂(propargyl) — 4-111NHCO₂Bu-t Me 2-Cl 4-112 NHCO₂Bu-t Me 3-Cl 4-113 NHCO₂Bu-t Me 4-Cl 4-114NHCO₂Bu-t Me 2,4-Cl₂ 4-115 NHCO₂Bu-t Me 3,5-Cl₂ 4-116 NHCO₂Bu-t Me3,4,5- Cl₃ 4-117 NHCO₂Bu-t Me 2-Me 4-118 NHCO₂Bu-n NH₂ — 4-119 NHCO₂Bu-nNHCO₂Bu-t — 4-120 NHCO₂CH₂CF₃ Me — 4-121 NHCO₂C₂F₅ Me — 4-122NHCO₂CH₂CH₂F Me — 4-123 NHCO₂C(CH₃)₂CF₃ Me — 4-124 NHCO₂CH₂CH₂CF₃ Me —4-125 NHCO₂CH₂C₂F₅ Me — 4-126 NHCO₂CH₂CH═CH₂ Me — 4-127 NHCO₂CH₂CH═CMe₂Me 4-128 NHCO₂C(CH₃)₂CH═CH₂ Me — 4-129 NHCO₂C(CH₃)₂CH═CHCH₃ Me — 4-130NHCO₂CH₂CH═CHCl Me — 4-131 NHCO₂CH₂CH═CHCF₃ Me — 4-132 NHCO₂CH₂CI═CI₂ Me— 4-133 NHCO₂(1,1-dimethyl-2- Me — propynyl) 4-134 NHCO₂(2-butynyl) Me —4-135 NHCO₂(1,1-dimethyl-2- Me — butynyl) 4-136 NHCO₂(1,1-dimethyl-2- Me— pentynyl) 4-137 NHCO₂(1-propynyl) Me — 4-138NHCO₂(1,1-dimethyl-3-Iodo- Me — 2-pentynyl) 4-139NHCO₂(4,4,4-trifluoro-2- Me — butynyl) 4-140 NHCO₂Pr-c Me — 4-141NHCO₂Hex-c Me — 4-142 NHCO₂CH₂CH₂NHCO₂Bu-t Me — 4-143 NHCO₂CH₂CH₂NHCO₂EtMe — 4-144 NHCO₂CH₂CH₂CH₂NHCOCH₃ Me — 4-145 NHCO₂CH₂CH₂CH₂NHMe₂ Me —4-146 NHCO₂CH₂CH₂N(Me)COCH₃ Me — 4-147 NHCO₂CH₂CH₂NHCOPh Me — 4-148NHCO₂CH₂CH₂N(Me)COPh Me — 4-149 NHCO₂CH₂CH₂NHPh Me — 4-150NHCO₂(CH₂)₄NH₂ Me — 4-151 NHCO₂CH₂NHCH₂Ph Me — 4-152 NHCO₂CH₂N(CH₂Ph) Me— (CO₂Bu-t) 4-153 NHCO₂CH₂C₃H₅-c Me — 4-154 NHCO₂CH(CH₃)C₃H₅-c Me —4-155 NHCO₂CH₂C₆H₁₁-c Me — 4-156 NHCO₂CH₂Ph Me — 4-157 NHCO₂CH(CH₃)CH₂PhMe — 4-158 NHCO₂CH(CH₃)Ph Me — 4-159 NHCO₂C(CH₃)₂Ph Me — 4-160NHCO₂CH₂C₆H₄CF₃-4 Me — 4-161 NHCO₂CH₂C₆H₄CN-4 Me — 4-162NHCO₂CH₂C₆H₄CN-3 Me — 4-163 NHCO₂CH₂C₆H₄Cl-4 Me — 4-164 NHCO₂CH₂C₆H₄Cl-3Me — 4-165 NHCO₂CH₂C₆H₄OMe-3 Me — 4-166 NHCO₂CH₂C₆H₄OMe-2 Me — 4-167NHCO₂CH₂C₆H₄Me-4 Me — 4-168 NHCO₂CH₂C₆H₄Me-3 Me — 4-169 NHCO₂CH₂C₆H₄Me-2Me — 4-170 NHCO₂CH₂C₆H₄SO₂Me-4 Me — 4-171 NHCO₂CH₂C₆H₄SO₂Me-3 Me — 4-172NHCO₂CH₂C₆H₄Ph-4 Me — 4-173 NHCO₂CH₂C₆H₄Ph-3 Me — 4-174 NHCO₂CH₂Py-2 Me— 4-175 NHCO₂CH₂(6-Me-2-Py) Me — 4-176 NHCO₂C(CH₃)₂Py-4 Me — 4-177NHCO₂CH₂(2-thiazolyl) Me — 4-178 NHCO₂CH₂(2-benzthiazolyl) Me — 4-179NHCO₂CH₂CH₂OMe Me — 4-180 NHCO₂CH₂CH₂OEt Me — 4-181 NHCO₂CH₂CH₂OPr-i Me— 4-182 NHCO₂CH₂CH₂OBu-i Me — 4-183 NHCO₂CH₂CH₂OCH₂CH₂OMe Me — 4-184NHCO₂CH₂CH₂OEt i-Pr — 4-185 NHCO₂CH₂CH₂OC₆H₄Cl-4 Me — 4-186 NHCOCH₂OPhMe — 4-187 NHCOCH₂OC₆H₄F-3 Me — 4-188 NHCOCH₂OC₆H₄OCF₃-3 Me — 4-189NHCO₂CH₂CH₂OCH₂Ph Me — 4-190 NHCO₂CH₂CH₂OCH₂CH₂Ph Me — 4-191NHCO₂(1,1-dimethyl-3- Me — phenyl-2-pentynyl) 4-192 NHCO₂(CH₂)₄SMe Me —4-193 NHCO₂(CH₂)₄SCF₃ Me — 4-194 NHCO₂(CH₂)₄SPh Me — 4-195NHCO₂(CH₂)₄SOMe Me — 4-196 NHCO₂(CH₂)₄SOCF₃ Me — 4-197 NHCO₂(CH₂)₄SOPhMe — 4-198 NHCO₂(CH₂)₄SO₂Me Me — 4-199 NHCO₂(CH₂)₄SO₂CF₃ Me — 4-200NHCO₂(CH₂)₄SO₂Ph Me — 4-201 NHCO₂Ph Me — 4-202 NHCO₂C₆H₄OMe-4 Me — 4-203NHCONHMe Me — 4-204 NHCONHC₂H₅ Me — 4-205 NHCONHPr-n Me — 4-206NHCONHBu-t Me — 4-207 NHCONHBu-s Me — 4-208 NHCONH(Hex-n) Me — 4-209 HCl — 4-210 NH₂ Cl — 4-211 NHCHO Cl — 4-212 NHCOCH₂CF₃ Cl — 4-213NHCOC₂F₅ Cl — 4-214 NHCOCH₂CH₂F Cl — 4-215 NHCOC(CH₃)₂CF₃ Cl — 4-216NHCOCH₂CH₂CF₃ Cl — 4-217 NHCOCH₂C₂F₅ Cl — 4-218 NHCOCH₂CH═CH₂ Cl — 4-219NHCOCH₂CH═CMe₂ Cl — 4-220 NHCOC(CH₃)₂CH═CH₂ Cl — 4-221NHCOC(CH₃)₂CH═CHCH₃ Cl — 4-222 NHCOCH₂CH═CHCl Cl — 4-223 NHCOCH₂CH═CHCF₃Cl — 4-224 NHCOCH₂CI═CI₂ Cl — 4-225 NHCO(1,1-dimethyl-2- Cl — propynyl)4-226 NHCO(2-butynyl) Cl — 4-227 NHCO(1,1-dimethyl-2- Cl — butynyl)4-228 NHCO(1,1-dimethyl-2- Cl — pentynyl) 4-229 NHCO(1-propynyl) Cl —4-230 NHCO(1,1-dimethyl-3-Iodo- Cl — 2-pentynyl) 4-231NHCO(4,4,4-trifluoro-2- Cl — butynyl) 4-232 NHCOPr-c Cl — 4-233NHCOHex-c Cl — 4-234 NHCO(CH₂)₄CO₂H Cl — 4-235 NHCOCH₂CH₂NHCO₂Bu-t Cl —4-236 NHCOCH₂CH₂NHCO₂Et Cl — 4-237 NHCOCH₂CH₂CH₂NHCOCH₃ Cl — 4-238NHCOCH₂CH₂CH₂NHMe₂ Cl — 4-239 NHCOCH₂CH₂N(Me)COCH₃ Cl — 4-240NHCOCH₂CH₂NHCOPh Cl — 4-241 NHCOCH₂CH₂N(Me)COPh Cl — 4-242NHCOCH₂CH₂NHPh Cl — 4-243 NHCO(CH₂)₄NH₂ Cl — 4-244 NHCOCH₂NHCH₂Ph Cl —4-245 NHCOCH₂N(CH₂Ph) Cl — (CO₂Bu-t) 4-246 NHCOCH₂CH₂OC₆H₄Cl-4 Cl —4-247 NHCOCH₂OPh Cl — 4-248 NHCOCH₂OC₆H₄F-3 Cl — 4-249NHCOCH₂OC₆H₄OCF₃-3 Cl — 4-250 NHCO(CH₂)₄SMe Cl — 4-251 NHCOCH₂CH₂OEt Cl— 4-252 NHCOCH₂CH₂OPr-i Cl — 4-253 NHCOCH₂CH₂OBu-i Cl — 4-254NHCOCH₂CH₂OCH₂CH₂OMe Cl — 4-255 NHCO₂CH₃ Cl — 4-256 NHCO₂C₂H₅ Cl — 4-257NHCO₂Pr-n Cl — 4-258 NHCO₂Pr-i Cl — 4-259 NHCO₂Bu-n Cl — 4-260 NHCO₂Bu-iCl — 4-261 NHCO₂Bu-s Cl — 4-262 NHCO₂Bu-t Cl — 4-263 NHCO₂Bu-t Br —4-264 NHCO₂Bu-t Cl 2-Cl 4-265 NHCO₂Bu-t Cl 3-Cl 4-266 NHCO₂Bu-t Cl 4-Cl4-267 NHCO₂Bu-t Cl 2,4-Cl₂ 4-268 NHCO₂Bu-t Cl 3,5-Cl₂ 4-269 NHCO₂Bu-t Cl3,4,5- Cl₃ 4-270 NHCO₂Bu-t Cl 2-Me 4-271 NHCO₂CH₂CF₃ Cl — 4-272NHCO₂C₂F₅ Cl — 4-273 NHCO₂CH₂CH₂F Cl — 4-274 NHCO₂C(CH₃)₂CF₃ Cl — 4-275NHCO₂CH₂CH₂CF₃ Cl — 4-276 NHCO₂CH₂C₂F₅ Cl — 4-277 NHCO₂CH₂CH═CH₂ Cl —4-278 NHCO₂CH₂CH═CMe₂ Cl — 4-279 NHCO₂C(CH₃)₂CH═CH₂ Cl — 4-280NHCO₂C(CH₃)₂CH═CHCH₃ Cl — 4-281 NHCO₂CH₂CH═CHCl Cl — 4-282NHCO₂CH₂CH═CHCF₃ Cl — 4-283 NHCO₂CH₂CI═CI₂ Cl — 4-284NHCO₂(1,1-dimethyl-2- Cl — propynyl) 4-285 NHCO₂(2-butynyl) Cl — 4-286NHCO₂(1,1-dimethyl-2- Cl — butynyl) 4-287 NHCO₂(1,1-dimethyl-2- Cl —pentynyl) 4-288 NHCO₂(1-propynyl) Cl — 4-289 NHCO₂(1,1-dimethyl-3-Iodo-Cl — 2-pentynyl) 4-290 NHCO₂(4,4,4-trifluoro-2- Cl — butynyl) 4-291NHCO₂Pr-c Cl — 4-292 NHCO₂Hex-c Cl — 4-293 NHCO₂CH₂CH₂NHCO₂Bu-t Cl —4-294 NHCO₂CH₂CH₂NHCO₂Et Cl — 4-295 NHCO₂CH₂CH₂CH₂NHCOCH₃ Cl — 4-296NHCO₂CH₂CH₂CH₂NMe₂ Cl — 4-297 NHCO₂CH₂CH₂N(Me)COCH₃ Cl — 4-298NHCO₂CH₂CH₂NHCOPh Cl — 4-299 NHCO₂CH₂CH₂N(Me)COPh Cl — 4-300NHCO₂CH₂CH₂NHPh Cl — 4-301 NHCO₂(CH₂)₄NH₂ Cl — 4-302 NHCO₂CH₂NHCH₂Ph Cl— 4-303 NHCO₂CH₂N(CH₂Ph) Cl — (CO₂Bu-t) 4-304 NHCO₂CH₂C₃H₅-c Cl — 4-305NHCO₂CH(CH₃)C₃H₅-c Cl — 4-306 NHCO₂CH₂C₆H₁₁-c Cl — 4-307 NHCO₂CH₂Ph Cl —4-308 NHCO₂CH(CH₃)CH₂Ph Cl — 4-309 NHCO₂CH(CH₃)Ph Cl — 4-310NHCO₂C(CH₃)₂Ph Cl — 4-311 NHCO₂CH₂C₆H₄CF₃-4 Cl — 4-312 NHCO₂CH₂C₆H₄CN-4Cl — 4-313 NHCO₂CH₂C₆H₄CN-3 Cl — 4-314 NHCO₂CH₂C₆H₄Cl-4 Cl — 4-315NHCO₂CH₂C₆H₄Cl-3 Cl — 4-316 NHCO₂CH₂C₆H₄OMe-3 Cl — 4-317NHCO₂CH₂C₆H₄OMe-2 Cl — 4-318 NHCO₂CH₂C₆H₄Me-4 Cl — 4-319NHCO₂CH₂C₆H₄Me-3 Cl — 4-320 NHCO₂CH₂C₆H₄Me-2 Cl — 4-321NHCO₂CH₂C₆H₄SO₂Me-4 Cl — 4-322 NHCO₂CH₂C₆H₄SO₂Me-3 Cl — 4-323NHCO₂CH₂C₆H₄Ph-4 Cl — 4-324 NHCO₂CH₂C₆H₄Ph-3 Cl — 4-325 NHCO₂CH₂Py-2 Cl— 4-326 NHCO₂CH₂(6-Me-2-Py) Cl — 4-327 NHCO₂C(CH₃)₂Py-4 Cl — 4-328NHCO₂CH₂(2-thiazolyl) Cl — 4-329 NHCO₂CH₂(2-benzthiazolyl) Cl — 4-330NHCO₂CH₂CH₂OMe Cl — 4-331 NHCO₂CH₂CH₂OEt Cl — 4-332 NHCO₂CH₂CH₂OPr-i Cl— 4-333 NHCO₂CH₂CH₂OBu-i Cl — 4-334 NHCO₂CH₂CH₂OCH₂CH₂OMe Cl — 4-335NHCO₂CH₂CH₂OC₆H₄Cl-4 Cl — 4-336 NHCOCH₂OPh Cl — 4-337 NHCOCH₂OC₆H₄F-3 Cl— 4-338 NHCOCH₂OC₆H₄OCF₃-3 Cl — 4-339 NHCO₂CH₂CH₂OCH₂Ph Cl — 4-340NHCO₂(1,1-dimethyl-3- Cl — phenyl-2-pentynyl) 4-341 NHCO₂CH₂CH₂OCH₂CH₂PhCl — 4-342 NHCO₂(1,1-dimethyl-3- Cl — phenyl-2-pentynyl) 4-343NHCO₂(CH₂)₄SMe Cl — 4-344 NHCO₂(CH₂)₄SCF₃ Cl — 4-345 NHCO₂(CH₂)₄SPh Cl —4-346 NHCO₂(CH₂)₄SOMe Cl — 4-347 NHCO₂(CH₂)₄SOCF₃ Cl — 4-348NHCO₂(CH₂)₄SOPh Cl — 4-349 NHCO₂(CH₂)₄SO₂Me Cl — 4-350 NHCO₂(CH₂)₄SO₂CF₃Cl — 4-351 NHCO₂(CH₂)₄SO₂Ph Cl — 4-352 NHCO₂Ph Cl — 4-353 NHCO₂C₆H₄OMe-4Cl — 4-354 NHCONHMe Cl — 4-355 NHCONHC₂H₅ Cl — 4-356 NHCONHPr-n Cl —4-357 NHCONHBu-t Cl — 4-358 NHCONHBu-s Cl — 4-359 NHCONH(Hex-n) Cl —4-360 NHCOCH₂CF₃ — — 4-361 NHCOC₂F₅ — — 4-362 NHCOCH₂CH₂F — — 4-363NHCOC(CH₃)₂CF₃ — — 4-364 NHCOCH₂CH₂CF₃ — — 4-365 NHCOCH₂C₂F₅ — — 4-366NHCOCH₂CH═CH₂ — — 4-367 NHCOCH₂CH═CMe₂ — — 4-368 NHCOC(CH₂)₂CH═CH₂ — —4-369 NHCOC(CH₃)₂CH═CHCH₃ — — 4-370 NHCOCH₂CH═CHCl — — 4-371NHCOCH₂CH═CHCF₃ — — 4-372 NHCOCH₂CI═CI₂ — — 4-373 NHCO(1,1-dimethyl-2- —— propynyl) 4-374 NHCO(2-butynyl) — — 4-375 NHCO(1,1-dimethyl-2- — —butynyl) 4-376 NHCO(1,1-dimethyl-2- — — pentynyl) 4-377 NHCO(1-propynyl)— — 4-378 NHCO(1,1-dimethyl-3-Iodo- — — 2-pentynyl) 4-379NHCO(4,4,4-trifluoro-2- — — butynyl) 4-380 NHCO(CH₂)₄CO₂H — — 4-381NHCOCH₂CH₂CH₂NHMe₂ — — 4-382 NHCO(CH₂)₄NH₂ — — 4-383 NHCOCH₂NHCH₂Ph — —4-384 NHCOCH₂N(CH₂Ph) — — (CO₂Bu-t) 4-385 NHCOCH₂CH₂NMe₂ — — 4-386NHCOCH₂CH₂NHEt — — 4-387 NHCOCH₂CH₂NHPr-n — — 4-388 NHCOCH₂CH₂OC₆H₄Cl-4— — 4-389 NHCOCH₂OPh — — 4-390 NHCOCH₂OC₆H₄F-3 — — 4-391NHCOCH₂OC₆H₄OCF₃-3 — — 4-392 NHCOCH2OC₆H₄CN-2 — — 4-393 NHCOCH2OC₆H₄F-4— — 4-394 NHCOCH₂OC₆H₃(3,4- — — methylenedioxy) 4-395NHCOCH₂OC₆H₄(CONH₂)-2 — — 4-396 NHCOCH₂OC₆H₃(3,4-(OCH₃)₂) — — 4-397NHCOCH₂O(6-CF₃- — — pyrimidin-4-yl) 4-398 NHCOCH₂O(3-Py) — — 4-399NHCOCH₂CH₂CH₂COCH₃ — — 4-400 NHCO₂CH₂CF₃ — — 4-401 NHCO₂C₂F₅ — — 4-402NHCO₂CH₂CH₂F — — 4-403 NHCO₂C(CH₃)₂CF₃ — — 4-404 NHCO₂CH₂CH₂CF₃ — —4-405 NHCO₂CH₂C₂F₅ — — 4-406 NHCO₂CH₂CH═CH₂ — — 4-407 NHCO₂CH₂CH═CMe₂ —— 4-408 NHCO₂C(CH₃)₂CH═CH₂ — — 4-409 NHCO₂C(CH₃)₂CH═CHCH₃ — — 4-410NHCO₂CH₂CH═CHCl — — 4-411 NHCO₂CH₂CH═CHCF₃ — — 4-412 NHCO₂CH₂CI═CI₂ — —4-413 NHCO₂(1,1-dimethyl-2- — — propynyl) 4-414 NHCO₂(2-butynyl) — —4-415 NHCO₂(1,1-dimethyl-2- — — butynyl) 4-416 NHCO₂(1,1-dimethyl-2- — —pentynyl) 4-417 NHCO₂(1-propynyl) — — 4-418 NHCO₂(1,1-dimethyl-3-Iodo- —— 2-pentynyl) 4-419 NHCO₂(4,4,4-trifluoro-2- — — butynyl) 4-420NHCO₂(1,1-dimethyl-3- — — phenyl-2-pentynyl) 4-421 NHCO₂CH₂CH₂NHCO₂Bu-t— — 4-422 NHCO₂CH₂CH₂NHCO₂Et — — 4-423 NHCO₂CH₂N(CH₂Ph) — — (CO₂Bu-t)4-424 NHCO₂CH₂NCH₂Ph — — 4-425 NHCO₂CH₂CH₂NCH₂Ph — — 4-426NHCO₂CH₂CH₂NCH₂C₆H₄Cl-4 — — 4-427 NHCO₂CH₂CH₂NHMe — — 4-428NHCO₂CH₂C(CH₃)₂N(CH₃)₂ — — 4-429 NHCO₂CH(CH₃)CH₂N(CH₃)₂ — — 4-430NHCO₂CH₂C₃H₅-c — — 4-431 NHCO₂CH(CH₃)C₃H₅-c — — 4-432 NHCO₂CH₂C₆H₁₁-c4-433 NHCO₂CH(CH₃)CH₂Ph — — 4-434 NHCO₂CH(CH₃)Ph — — 4-435NHCO₂C(CH₃)₂Ph — — 4-436 NHCO₂CH₂C₆H₄CF₃-4 — — 4-437 NHCO₂CH₂C₆H₄CN-4 —— 4-438 NHCO₂CH₂C₆H₄CN-3 — — 4-439 NHCO₂CH₂C₆H₄Cl-4 — — 4-440NHCO₂CH₂C₆H₄Cl-3 — — 4-441 NHCO₂CH₂C₆H₄OMe-3 — — 4-442 NHCO₂CH₂C₆H₄OMe-2— — 4-443 NHCO₂CH₂C₆H₄Me-4 — — 4-444 NHCO₂CH₂C₆H₄Me-3 — — 4-445NHCO₂CH₂C₆H₄Me-2 — — 4-446 NHCO₂CH₂C₆H₄SO₂Me-4 — — 4-447NHCO₂CH₂C₆H₄SO₂Me-3 — — 4-448 NHCO₂CH₂C₆H₄Ph-4 — — 4-449NHCO₂CH₂C₆H₄Ph-3 — — 4-450 NHCO₂CH₂C₆H₄OCH₃-4 — — 4-451NHCO₂CH₂C₆H₃(3,4- — — methylenedioxy) 4-452 NHCO₂CH₂Py-2 — — 4-453NHCO₂CH₂(6-Me-2-Py) — — 4-454 NHCO₂C(CH₃)₂Py-4 — — 4-455NHCO₂CH₂(2-thiazolyl) — — 4-456 NHCO₂CH₂(2-benzthiazolyl) — — 4-457NHCO₂CH₂(3-Py) — — 4-458 NHCO₂CH₂(4-Py) — — 4-459 NHCO₂CH(CH₃)(4-Py) — —4-460 NHCO₂CH₂CH₂OMe — — 4-461 NHCO₂CH₂CH₂OEt — — 4-462 NHCO₂CH₂CH₂OPr-i— — 4-463 NHCO₂CH₂CH₂OBu-i — — 4-464 NHCO₂CH₂CH₂OCH₂CH₂OMe — — 4-465NHCO₂C(CH₃)₂CH₂OCH₃ — — 4-466 NHCO₂CH(CH₃)CH₂OCH₃ — — 4-467NHCO₂CH₂CH₂OC₆H₄Cl-4 — — 4-468 NHCO₂CH₂OPh — — 4-469 NHCO₂CH₂OC₆H₄F-3 —— 4-470 NHCO₂CH₂OC₆H₄OCF₃-3 — — 4-471 NHCO₂CH₂CH₂OCH₂Ph — — 4-472NHCO₂CH₂CH₂OCH₂CH₂Ph — — 4-473 NHCO₂(CH₂)₄SMe — — 4-474 NHCO₂(CH₂)₄SCF₃— — 4-475 NHCO₂(CH₂)₄SPh — — 4-476 NHCO₂(CH₂)₄SOMe — — 4-477NHCO₂(CH₂)₄SOCF₃ — — 4-478 NHCO₂(CH₂)₄SOPh — — 4-479 NHCO₂(CH₂)₄SO₂Me —— 4-480 NHCO₂(CH₂)₄SO₂CF₃ — — 4-481 NHCO₂(CH₂)₄SO₂Ph — — 4-482 NHCO₂Ph —— 4-483 NHCO₂C₆H₄OMe-4 — —

Among the compounds shown in Tables 1 to 4, the spectral data (¹H-NMR(300 MHz, CDCl₃)) of some compounds are as shown in Table 5.

TABLE 5 No NMR Data 1-3 1.24 (s, 9H), 4.01 (s, 3H), 4.37 (br-s, 2H),5.21 (s, 2H), 6.41 (d, 1H, J = 1.1 Hz), 6.63 (d, 1H, J = 1.1 Hz),7.34-7.44 (m, 3H), 7.53-7.56 (m, 2H). 1-4 1.38 (t, 3H, J = 7.0 Hz),3.97-4.04 (m, 2H), 4.01 (s, 3H), 4.35 (br-s, 2H), 5.16 (s, 2H), 5.88 (d,1H, J = 2.0 Hz), 6.20 (d, 1H, J = 2.0 Hz), 7.35-7.44 (m, 3H), 7.52-7.55(m, 2H). 1-5 2.19 (s, 3H), 3.96 (s, 3H), 4.29 (br-s, 2H), 5.27 (s, 2H),6.42 (d, 1H, J = 8.2 Hz), 7.23-7.26 (m, 1H), 7.34-7.46 (m, 3H),7.51-7.54 (m, 2H). 1-6 3.77 (s, 3H), 4.00 (s, 3H), 4.40 (br-s, 2H), 5.16(s, 2H), 5.89 (s, 1H), 6.21 (s, 1H), 7.34-7.54 (m, 5H) 1-7 1.19 (t, 3H),2.52 (q, 2H), 4.00 (s, 3H), 4.45 (br-s, 2H), 5.19 (s, 2H), 6.29 (s, 1H),6.47 (s, 1H), 7.34-7.55 (m, 5H) 1-17 1.33 (s, 9H), 3.85 (s, 3H), 3.99(s, 3H), 5.20 (s, 2H), 6.54 (d, 1H, J = 2.1 Hz), 7.34-7.53 (m, 5H), 7.82(d, 1H, J = 2.1 Hz), 7.95 (br-s, 1H). 1-71 1.52 (s, 9H), 2.33 (s, 3H),3.97 (s, 3H), 5.21 (s, 2H), 6.75 (s, 1H), 7.13 (br-s, 1H), 7.34-7.54 (m,5H), 7.71 (s, 1H). 1-73 1.53 (s, 9H), 3.98 (s, 3H), 5.24 (s, 2H), 5.48(d, 1H, J = 11.1 Hz), 5.99 (d, 1H, J = 17.7 Hz), 6.65 (dd, 1H, J = 17.7,11.1 Hz), 6.95 (s, 1H), 7.20 (br-s, 1H), 7.35-7.53 (m, 5H), 7.88 (s,1H). 1-76 1.22 (t, 3H, J = 7.0 Hz), 1.51 (s, 9H), 3.58 (q, 2H, J = 7.0Hz), 3.78 (t, 2H, J = 4.7 Hz), 3.98 (s, 3H), 4.18 (t, 2H, J = 4.7 Hz),5.17 (s, 2H), 6.52 (d, 1H, J = 2.2 Hz), 7.25 (br-s, 1H), 7.34-7.53 (m,6H). 1-77 1.31 (d, 6H, J = 7.8 Hz), 1.51 (s, 9H), 3.98 (s, 3H), 4.66(hept, 1H, J = 7.8 Hz), 5.17 (s, 2H), 6.42 (d, 1H, J = 1.8 Hz), 7.22(br-s, 1H), 7.34-7.53 (m, 6H). 1-78 0.96 (t, 3H, J = 7.2 Hz), 1.41-1.48(m, 2H), 1.52 (s, 9H), 1.71-1.80 (m, 2H), 3.98 (s, 3H), 4.03 (t, 2H, J =6.6 Hz), 5.19 (s, 2H), 6.47 (d, 1H, J = 1.8 Hz), 7.34-7.62 (m, 7H). 1-821.51(s, 9H), 3.00(s, 6H), 3.98(s, 3H), 5.16(s, 2H), 6.15(d, 1H),7.02(brs, 1H), 7.11(d, 1H), 7.37-7.44(m, 3H), 7.52-7.55(m, 2H) 1-83 1.49(s, 9H), 1.52 (s, 9H), 3.30 (s, 3H), 4.01 (s, 3H), 5.21 (s, 2H), 7.12(d, 1H, J = 1.9 Hz), 7.14 (br-s, 1H), 7.35-7.55 (m, 5H), 7.80 (d, 1H, J= 1.9 Hz). 1-86 1.51 (s, 9H), 3.31 (t, 4H, J = 4.9 Hz), 3.81 (t, 4H, J =4.9 Hz), 3.99 (s, 3H), 5.17 (s, 2H), 6.30 (d, 1H, J = 2.2 Hz), 7.16(br-s, 1H), 7.32-7.65 (m, 6H). 1-89 1.53 (s, 9H), 3.87 (s, 3H), 4.03 (s,3H), 5.70 (s, 2H), 7.34-7.55 (m, 5H), 7.77 (br-s, 1H), 7.93 (d, 1H),8.21 (d, 1H). 1-90 1.54 (s, 9H), 3.99 (s, 3H), 5.28 (s, 2H), 7.15 (s,1H), 7.35-7.51 (m, 6H), 8.18 (s, 1H). 1-131 0.95(t, 3H, J = 7.3 Hz),1.37-1.44(m, 2H), 1.60-1.70(m, 2H), 3.99(s, 3H), 4.16(t, 2H, J = 6.7Hz), 4.25(br-s, 2H), 5.14(s, 2H), 6.18(d, 1H, J = 2.0 Hz), 7.16(d, 1H, J= 2.0 Hz), 7.35-7.47(m, 3H), 7.51-7.54(m, 2H) 1-132 0.95(t, 3H, J = 7.4Hz), 1.41(tq, 2H, J = 7.6, 7.4 Hz), 1.51 or 1.55(s, 9H), 1.66(tt, 2H, J= 7.6, 6.7 Hz), 4.03(s, 3H), 4.18(t, 2H, J = 6.7 Hz), 5.20(s, 2H),6.72(br-s, 1H), 7.20(br-s, 1H), 7.35-7.54(m, 5H), 7.78(d, 1H, J = 1.8Hz) 1-197 1.23 (t, 3H), 1.24 (d, 6H), 2.90 (septet, 1H), 3.55 (q, 2H),3.69(t, 2H), 3.99 (s, 3H), 4.34 (t, 2H), 5.23 (s, 2H), 6.82 (s, 1H),7.35-7.54 (m, 6H), 7.79 (s, 1H). 1-275 1.52(s, 9H), 3.99(s, 3H), 5.20(s,2H), 6.94(d, 1H, J = 1.6 Hz), 7.20(br-s, 1H), 7.35-7.52(m, 5H), 7.96(d,1H, J = 1.5 Hz) 1-278 1.53 (s, 9H), 3.99 (s, 3H), 5.19 (s, 2H), 7.09 (s,1H), 7.15 (br-s, 1H), 7.36-7.51 (m, 5H), 8.13 (s, 1H) 1-377 4.00 (s,3H), 5.31 (s, 2H), 7.15 (d, 1H), 7.36-7.51 (m, 6H), 7.80 (dd, 1H), 8.12(d, 1H), 8.65 (br-s, 1H). 1-398 in CD₃0D 1.34-1.70 (m, 6H), 2.37 (t,2H), 2.84 (t, 2H), 3.92 (s, 3H), 4.59 (br-s, 2H), 5.21 (s, 2H), 7.02 (d,1H), 7.29-7.67 (m, 6H), 7.70 (t, 1H), 7.93 (d, 1H) 1-399 2.13 (br-s,1H), 3.45 (s, 2H), 3.87 (s, 2H), 3.97 (s, 3H), 5.30 (s, 2H), 7.02 (d,1H), 7.23-7.54 (m, 10H), 7.70 (t, 1H), 8.17 (d, 1H), 9.69 (br-s, 1H)1-400 1.47 (s, 9H), 3.98 (s, 3H), 4.52 (d, 2H), 4.58 (s, 2H), 5.27 (s,2H), 7.02 (d, 1H), 7.26-7.52 (m, 11H), 7.71 (t, 1H), 8.14 (d, 1H) 1-4053.95 (s, 3H), 4.64 (s, 3H), 5.30 (s, 3H), 7.01 (d, 1H), 7.02-7.08 (m,2H), 7.32-7.53 (m, 8H), 7.74 (t, 1H), 8.22 (d, 1H), 8.87 (br-s, 1H).1-411 4.03 (s, 3H), 4.75 (s, 2H), 5.31 (s, 2H), 7.01 (d, 1H), 7.07 (d,1H), 7.16 (t, 1H), 7.37-7.67 (m, 7H), 7.34 (t, 1H), 8.17 (d, 1H), 8.86(s, 1H). 1-415 3.99 (s, 3H), 4.58 (q, 2H, JC-F = 8.3 Hz), 5.72 (s, 2H),7.01 (d, 1H, J = 7.7 Hz), 7.35-7.52 (m, 6H), 7.72 (dd, 1H, J = 8.1, 7.7Hz), 7.86 (d, 1H, J = 8.1 Hz). 1-418 1.76 (s, 6H), 3.98 (s, 3H), 5.26(s, 2H), 6.97 (d, 1H), 7.34-7.52 (m, 6H), 7.68 (t, 1H), 7.80 (d, 1H)1-420 3.99 (s, 3H), 4.66 (t, 2H), 5.27 (s, 2H), 7.01 (d, 1H), 7.33-3.54(m, 6H), 7.73 (dd, 1H), 7.86 (d, 1H). 1-421 3.98 (s, 3H), 4.69 (d, 2H, J= 5.7 Hz), 5.26 (s, 2H), 5.27 (d, 1H, J = 10.8 Hz), 5.37 (d, 1H, J =17.3 Hz), 5.97 (ddt, 1H, 17.3, 10.8, 5.7 Hz), 6.96 (d, 1H, J = 7.5 Hz),7.31-7.52 (m, 6H), 7.68 (dd, 1H, J = 8.2, 7.5 Hz), 7.89 (d, 1H, 8.2 Hz).1-422 1.75 (s, 3H), 1.78 (s, 3H), 3.98 (s, 3H), 4.68 (d, 2H, J = 7.4Hz), 5.25 (s, 2H), 5.40 (tdd, 1H, J = 7.4, 1.4, 1.3 Hz), 6.95 (d, 1H, J= 7.6 Hz), 7.24 (br, 1H) , 7.34-7.53 (m, 5H), 7.67 (dd, 1H, J = 8.4, 7.6Hz), 7.90 (d, 1H, 8.4 Hz). 1-423 1.59 (s, 6H), 3.97 (s, 3H), 5.13 (d,1H), 5.23 (d, 1H), 5.25 (s, 2H), 6.15 (dd, 1H), 6.93 (d, 1H), 7.34-7.52(m, 6H), 7.64 (t, 1H), 7.86 (d, 1H) 1-424 1.33 (d, 3H), 1.74 (d, 6H),3.97 (s, 3H), 5.18-5.31 (m, 1H), 5.24 (s, 2H), 5.58-5.63 (m, 1H), 6.93(d, 1H), 7.19 (br-s, 1H), 7.35-7.55 (m, 5H), 7.66 (t, 1H), 7.89 (d, 1H)1-428 1.75 (s, 6H), 2.59 (s, 1H), 3.97 (s, 3H), 5.25 (s, 2H), 6.95 (d,1H), 7.34-7.52 (m, 6H), 7.64 (t, 1H), 7.93 (d, 1H). 1-430 1.71 (s, 6H),1.86 (s, 3H), 3.97 (s, 3H), 5.25 (s, 2H), 6.94 (d, 1H), 7.34-7.52 (m,6H), 7.66 (t, 1H), 7.92 (d, 1H) 1-431 1.13 (t, 3H), 1.72 (s, 6H), 2.23(q, 2H), 4.00 (s, 3H), 5.24 (s, 2H), 6.93 (d, 1H), 7.21 (br-s, 1H), 7.34(m, 5H), 7.66 (t, 1H), 7.92 (d, 1H) 1-435 1.84 (s, 6H), 3.97 (s, 3H),5.25 (s, 2H), 6.94 (d, 1H, J = 7.8 Hz), 7.24-7.52 (m, 11H), 7.66 (dd,1H, J = 8.1, 7.8 Hz), 7.92 (d, 1H, J = 8.1 Hz). 1-437 1.15 (t, 3H), 2.22(q, 2H), 3.59 (q, 2H), 3.98 (s, 3H), 4.30 (t, 2H), 5.26 (s, 2H), 5.96(br-s, 1H), 6.98 (d, 1H), 7.35-7.52 (m, 6H), 7.69 (t, 1H), 7.87 (d, 1H).1-443 1.10 (s, 6H), 2.32 (s, 6H), 3.98 (s, 3H), 4.10 (s, 2H), 5.25 (s,2H), 6.95 (d, 1H), 7.34-7.53 (m, 6H), 7.68 (t, 1H), 7.89 (d, 1H) 1-4441.30 (d, 3H), 2.29 (s, 6H), 2.60 (dd, 1H), 3.98 (s, 3H), 5.05 (tq, 1H),5.25 (s, 2H), 6.94 (d, 1H), 7.34-7.52 (m, 6H), 7.66 (t, 1H), 7.88 (d,1H) 1-445 0.30-0.35 (m, 2H), 0.57-0.63 (m, 2H), 1.14-1.24 (m, 1H), 3.98(s, 3H), 4.02 (d, 2H, J = 7.3 Hz), 5.26 (s, 2H), 6.96 (d, 1H, J = 7.1Hz), 7.28 (br, 1H), 7.35-7.53 (m, 5H), 7.68 (dd, 1H, J = 8.2, 7.1 Hz),7.89 (d, 1H, J = 8.2 Hz). 1-446 0.27-0.32 (m, 1H), 0.43-0.59 (m, 3H),1.01-1.04 (m, 1H), 1.36 (d, 3H), 3.98 (s, 3H), 4.33 (q, 1H), 5.26 (s,2H), 6.94 (d, 1H), 7.32-7.52 (m, 6H), 7.67 (t, 1H), 7.88 (d, 1H) 1-4481.30 (d, 3H), 2.82 (dd, 1H), 2.30 (dd, 1H), 3.97 (s, 3H), 5.13 (q, 1H),5.25 (s, 2H), 6.94 (d, 1H), 7.21-7.52 (m, 11H), 7.66 (t, 1H), 7.86 (d,1H) 1-449 1.61 (d, 3H), 3.97 (s, 3H), 5.24 (s, 2H), 5.89 (q, 1H), 6.94(d, 1H), 7.31-7.52 (m, 11H), 7.65 (t, 1H), 7.87 (d, 1H) 1-450 2.04 (s,6H), 3.97 (s, 3H), 5.25 (s, 2H), 6.91 (d, 1H), 7.23-7.52 (m, 11H), 7.58(t, 1H), 7.77 (d, 1H) 1-451 3.97 (s, 3H), 5.25 (s, 2H), 5.27 (s, 2H),6.97 (d, 1H), 7.34-7.71 (m, 11H), 7.88 (d, 1H) 1-456 3.81 (s, 3H), 3.97(s, 3H), 5.19 (s, 2H), 5.24 (s, 2H), 6.86-6.98 (m, 4H), 7.35-7.52 (m,7H), 7.68 (m, 1H), 7.90 (d, 1H, J = 8.1 Hz). 1-457 3.86 (s, 3H), 3.97(s, 3H), 5.24 (s, 2H), 5.28 (s, 2H), 6.89-6.98 (m, 3H), 7.30-7.52 (m,8H), 7.67 (m, 1H), 7.92 (d, 1H, J = 8.4 Hz). 1-465 3.81 (s, 3H), 3.96(s, 3H), 5.15 (s, 2H), 5.24 (s, 2H), 6.90 (m, 2H), 6.94 (d, 1H, J = 7.2Hz), 7.32-7.51 (m, 8H), 7.67 (m, 1H), 7.90 (d, 2H, J = 8.1 Hz). 1-4663.97 (s, 3H), 5.11 (s, 2H), 5.24 (s, 2H), 5.97 (s, 2H), 6.78-6.96 (m,4H), 7.34-7.52 (m, 6H), 7.68 (t, 1H), 7.90 (d, 1H) 1-467 3.98 (s, 3H),5.26 (s, 2H), 5.34 (s, 2H), 6.97 (d, 1H), 7.23-7.75 (m, 10H), 7.91 (d,1H), 8.61 (d, 1H) 1-470 3.98 (s, 3H), 5.26 (s, 2H), 5.52 (s, 2H), 6.99(d, 1H), 7.34-7.52 (m, 7H), 7.70 (t, 1H), 7.82 (br-s, 1H), 7.92 (d, 1H)1-471 3.99 (s, 3H), 5.27 (s, 2H), 5.61 (s, 2H), 6.99 (d, 1H), 7.34-7.68(m, 9H), 7.74 (dd, 1H), 7.91-7.93 (m, 1H), 8.05 (d, 1H). 1-474 1.60 (d,3H), 3.98 (s, 3H), 5.26 (s, 2H), 6.97 (d, 1H), 7.28-7.51 (m, 8H), 7.67(t, 1H), 7.84 (d, 1H), 8.60 (d, 2H) 1-477 1.19 (d, 6H, J = 5.9 Hz),3.59-3.69 (m, 3H), 3.98 (s, 3H), 4.32 (t, 2H, J = 4.8 Hz), 5.26 (s, 2H),6.96 (d, 1H, J = 7.6 Hz), 7.34-7.53 (m, 6H), 7.68 (dd, 1H, J = 8.1, 7.6Hz), 7.89 (d, 1H, J = 8.1 Hz). 1-480 1.52 (s, 6H), 3.41 (s, 3H), 3.56(s, 2H), 3.97 (s, 3H), 5.25 (s, 2H), 6.93 (d, 1H), 7.35-7.53 (m, 6H),7.65 (t, 1H), 7.85 (d, 1H). 1-481 1.31 (d, 3H), 3.39 (s, 3H), 3.47 (d,2H), 3.98 (s, 3H), 5.09 (tq, 1H), 5.25 (s, 2H), 6.95 (d, 1H), 7.34-7.52(m, 6H), 7.67 (t, 1H), 7.89 (d, 1H) 1-482 3.98 (s, 3H), 4.19 (t, 2H, J =4.7 Hz), 4.53 (t, 2H, J = 4.7 Hz), 5.25 (s, 2H), 6.85 (d, 2H, J = 9.0Hz), 6.97 (d, 1H, J = 7.5 Hz), 7.24 (d, 2H, J = 9.0 Hz), 7.34-7.52 (m,6H), 7.69 (dd, 1H, J = 8.6, 7.5 Hz), 7.88 (d, 1H, 8.6 Hz). 1-486 3.73(t, 2H, J = 4.8 Hz), 3.98 (s, 3H), 4.37 (t, 2H, J = 4.8 Hz), 4.58 (s,2H), 5.25 (s, 2H), 6.96 (d, 1H, J = 7.5 Hz), 7.29-7.53 (m, 11H), 7.68(dd, 1H, J = 8.6, 7.5 Hz), 7.88 (d, 1H, J = 8.6 Hz). 1-488 1.65-1.85 (m,4H), 2.11 (s, 3H), 2.54 (t, 2H, J = 7.0 Hz), 3.98 (s, 3H), 4.21 (t, 2H,J = 6.3 Hz), 5.26 (s, 2H), 6.96 (d, 1H, J = 7.5 Hz), 7.28 (s, 1H),7.34-7.53 (m, 5H), 7.68 (dd, 1H, J = 8.2, 7.5 Hz), 7.89 (d, 1H, J = 8.2Hz). 1-491 1.82-1.98 (m, 4H), 2.59 (s, 3H), 2.67-2.83 (m, 2H), 3.98 (s,3H), 4.24 (t, 2H, J = 5.8 Hz), 5.26 (s, 2H), 6.96 (d, 1H, J = 7.5 Hz),7.35-7.53 (m, 6H), 7.69 (dd, 1H, J = 8.4, 7.5 Hz), 7.88 (d, 1H, J = 8.4Hz). 2-68 1.53 (s, 6H), 2.42 (s, 3H), 3.89 (s, 3H), 5.18 (s, 2H),7.33-7.51 (m, 5H), 8.26 (br-s, 1H) 2-82 1.55 (s, 9H), 3.97 (s, 3H), 5.32(s, 2H), 7.35-7.52 (m, 5H), 8.69 (brs, 1H). 2-94 1.55 (s, 9H), 3.89 (s,3H), 5.29 (s, 2H), 7.33-7.49 (m, 10H), 8.67 (br-s, 1H). 2-399 2.00 (tt,2H), 2.16 (s, 3H), 2.49 (t, 2H), 2.59 (t, 2H), 3.95 (s, 3H), 5.25 (s,2H), 6.91 (s, 1H), 7.34-7.52 (m, 5H), 9.25 (br-s, 1H)

Each of the tetrazoyloxime derivatives represented by formula (1) orsalts thereof (hereinafter referred to as the “compound of the presentinvention”) has excellent fungicidal activity against wide range offungi belonging to, for example, Oomycetes, Ascomycetes, Deuteromycetesand Basidiomycetes. Therefore, the composition containing the compoundof the present invention as the active ingredient can be used forcontrolling various plant diseases infesting on agricultural andhorticultural crops including ornamental flowers, lawns and forage cropsby means of seed treatment, foliage application, soil application, orwater surface application.

For example, it is possible to use the composition containing thecompound of the present invention for controlling plant diseases shownbelow.

Sugar beet: Cercospora leaf spot (Cercospora beticola)

-   -   Aphanomyces root rot (Aphanomyces cochlioides)        Peanut: Brown leaf spot (Mycosphaerella arachidis)    -   Leaf spot (Mycosphaerella berkeleyi)        Cucumber: Powdery mildew (Sphaerotheca fuliginea)    -   Gummy stem blight (Mycosphaerella melonis)        Stem rot (Sclerotinia sclerotiorum)    -   Gray mold (Botrytis cinerea)    -   Scab (Cladosporium cucumerinum)    -   Downy mildew (Pseudoperonospora cubensis)        Tomato: Gray mold (Botrytis cinerea)    -   Leaf mold (Cladosporium fulvum)    -   Cottony leak (Phythium aphanidermatum)    -   Late blight (Phytophthora infestans)        Eggplant: Gray mold (Botrytis cinerea)    -   Black rot (Corynespora melongeneae)    -   Powdery mildew (Erysiphe cichoracearum)        Spinach Damping-off (Pythium ultimum)        Strawberry:    -   Gray mold (Botrytis cinerea)    -   Powdery mildew (Sphaerotheca aphanis)        Onion: Gray-mold neck rot (Botrytis allii)    -   Gray-mold (Botrytis cinerea)        Kidney bean:    -   Stem rot (Sclerotinia sclerotiorum)    -   Gray mold (Botrytis cinerea)        Apple: Powdery mildew (Podosphaera leucotricha)    -   Scab (Venturia inaequalis)    -   Blossom blight (Monilinia mali)        Persimon:    -   Powdery mildew (Phyllactinia kakicola)    -   Anthracnose (Gloeosporium kaki)    -   Angular leaf spot (Cercospora kaki)        Peach & Chemy:    -   Brown rot (Monilinia fructicola)        Grape: Gray mold (Botrytis cinerea)    -   Powdery mildew (Uncinula necator)    -   Ripe rot (Glomerella cingulata)    -   Downy mildew (Plasmopara viticola)        Pear: Scab (Venturia nashicola)    -   Rust (Gymnosporangium asiaticum)    -   Black spot (Alternaria kikuchiana)        Tea: Gray blight (Pestalotia theae)    -   Anthracnose (Colletotrichum theae-sinensis)        Citrus: Scab (Elsinoe fawcetti)    -   Blue mold (Penicillium italicum)    -   Common green mold (Penicillium digitatum)    -   Gray mold (Botrytis cinerea)        Barley: Powdery mildew (Erysiphe graminis f. sp. hordei)    -   Loose smut (Ustilago nuda)        Wheat: Scab (Gibberella zeae)    -   Leaf rust (Puccinia recondita)    -   Spot blotch (Cochliobolus sativus)        -   Glume blotch (Leptosohaeria nodorum)    -   Eye spot (Pseudocercosporella herpotrichoides)    -   Powdery mildew (Erysiphe graminis f. sp. tritici)    -   Snow mold (Micronectriella nivalis)    -   Browning root rot (Pythium iwayamai)        Rice:    -   Blast (Pyricularia oryzae)    -   Sheath blight (Rhizoctonia solani)    -   Bakanae disease (Gibberella fujikuroi)    -   Brown spot (Cochliobolus miyabeanus)    -   Seeding blight (Pythiym graminicolum)        Soybean: Purple speck of seed (Cercospora kikuchii)    -   Downy mildew (Peronospora manshurica) Phytophthora root rot        (Phytophthora sojae)        Potato: Late blight (Phytophthora infestans)        Cruciferous plants:    -   Clubroot (Plasmodiophora brassicae)        Tobacco: Stem rot (Sclerotinia sclerotiorum)    -   Powdery mildew (Erysiphe cichoracearum)        Tulip: Gray mold (Botrytis cinerea)        Bent grass: Sclerotinia snow blight (Sclerotinia borealis)    -   Pythium red blight (Pythium aphanidermatum)        Orchard grass:    -   Powdery mildew (Erysiphe graminis)

Besides, in recent years, various plant pathogenic fungi have developedresistance to phenylamide fungicides and strobilurin fungicides. Itfollows that there is a problem in the control of such a problematicplant disease, because no fungicide can control those plant diseasessufficiently. Therefore, an effective fungicide, which can control suchfungi being resistant against those problematic plant diseases isdesired. The compounds of the present invention are effective to thoseresistant strains of fungi to aforementioned fungicides as well assusceptible ones.

For example, the compounds of the present invention are also effectiveto those resistant strains of fungi to Late blight of potato and tomato(Phytophthora infestans), Downy mildew of cucumber (Pseudoperonosporacubensis) and Downy mildew of grape (Plasmopara viticola) which showresistance to metalaxyl, as well as susceptible ones.

Furthermore, the compounds of the present invention are also effectiveto Downy mildew of cucumber (Pseudoperonospora cubensis) and Downymildew of grape (Plasmopara viticola) which show resistance tostrobilurin fungicides (for example, kresoxim-methyl, azoxystrobin,etc.) similar to susceptible fungi.

Examples of preferred plant injury to which the compounds of the presentinvention are applied include various plant injuries caused by Oomycetessuch as Downy mildew of grape (Plasmopara viticola), Downy mildew ofgourds (Pseudoperonospora cubensis), Late blight of potato and tomato(Phytophthora infestans), Pythium disease of the grass (Pythiumaphanidermatum, etc.) and Black root of sugar beet (Aphanomycescochlloides).

Further, the compounds of the present invention can be used also as anantifouling agent which prevents water-dwelling organisms from adheringto structures placed in water such as the outer bottom of a vessel andfishing net.

Moreover, the intermediate chemical compounds of the chemical compoundsof the present invention may have fungicidal activities.

Also, the compounds of the present invention can be contained in paintsand fibers and thereby used as an antimicrobial and antifungal agent forwalls, bathtubs, shoes and clothes.

2) Plant Disease Controlling Agent

The second aspect of the present invention is directed to a plantdisease controlling agent containing the compound of the presentinvention as an active ingredient.

The plant disease controlling agent of the present invention can be usedin the state of the compounds of the present invention alone without theaddition of other ingredients or, for the use as agricultural chemicals,the compound can be applied in forms of general formulations foragricultural chemicals, such as wettable powders, granules, powders,emulsifiable concentrates, aqueous solutions, suspensions and flowables.

For the additives and carriers to be used in the plant diseasecontrolling agent of the present invention, vegetable powders such assoybean powder and wheat powder, mineral fine powders such asdiatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite andclay, and organic and inorganic compounds such as sodium benzoate, ureaand salt cake can be used, when the compounds are formulated into solidformulations.

When the compounds are formulated into liquid formulations, petroleumfractions such as kerosine, xylene and solvent naphtha, cyclohexane,cyclohexanone, dimethylformamide, dimethylsulfoxide, alcohol, acetone,trichloroethylene, methylisobutylketone, mineral oil, vegetable oil andwater, can be used as the solvent.

In the plant disease controlling agent of the present invention,surfactants may be added to the formulations in order to make theformulations homogeneous and stable, if appropriate.

Examples of the surfactants include nonionic surfactants such as alkylphenyl ether added with polyoxyethylene, alkyl ether added withpolyoxyethylene, higher fatty acid ester added with polyoxyethylene,sorbitan higher fatty acid ester added with polyoxyethylene,tristyrylphenyl ether added with polyoxyethylene; sulfuric ester salt ofalkyl phenyl ether added with polyoxyethylene, alkylbenzene sulfonatesalt, sulfuric ester salt of higher alcohol, alkylnaphthalene sulfonatesalt, polycarboxylate salt, lignin sulfonate salt, formaldehydecondensate of alkylnaphthalene sulfonate, and copolymer ofisobutylene-maleic anhydride.

In general, the content of an active ingredient in the formulations iswithin a range from 0.5 to 95% by weight, and preferably from 2 to 70%by weight, based on the total weight of the composition (formulation).

When the plant disease controlling agent of the present invention is inthe form of wettable powders, emulsifiable concentrates and flowableformulations, it can be applied in a form prepared by diluting theformulations with water to the suspension or the emulsion at a desiredconcentrations, while the powders and the granules of the said compoundcan be directly dispersed to plants.

Needless to say that the compound of the present invention or the plantdisease controlling agent of the present invention alone has sufficientfungicidal activity, however, it can be used in combination with onekind, two kinds, or more of various types of fungicides, insecticides,acaricides and synergists.

Typical examples for the fungicides, insecticides, acaricides and plantgrowth regulators, those which are usable in admixing with the compoundsof the present invention or the plant disease controlling agent of thepresent invention, are shown below.

Fungicides:

Copper agents: basic copper chloride, basic copper sulfate

Sulfur agents: thiuram, zineb, maneb, mancozeb, ziram, propineb,polycarbamate, etc.

Polyhaloalkylthio agents: captan, folpet, dichlorofluanid, etc.

Organic chlorine agents: chlorothalonil, fthalide, etc.

Organic phosphorous agents: IBP, EDDP, trichlophosmethyl, pyrazophos,fosetyl, etc.

Benzimidazole agents: thiophanate-methyl, benomyl, carbendazim,thiabendazole, etc.

Dicarboxylmide agents: iprodione, procymidone, vinclozolin, fluoroimide,etc.

Carboxyamide agents: oxycarboxin, mepronil, flutolanil, tecloftalam,trichlamide, pencycuron, etc.

Acylalanine agents: metalaxyl, oxadixyl, furalaxyl, etc.

Strobilurin-based agents: azoxystrobin, kresoxim-methyl, pyraclostrobin,trifloxystrobin, pyribencarb, famoxadone, fenamidone, etc.

Anilinopyrimidine agents: andoprin, mepanipyrim, pyrimethanil,diprozinil, etc.

SBI agents: triadimefon, triadimenol, bitertanol, myclobutanil,hexaconazole, propiconazole, triflumizole, prochloraz, pefurazoate,fenarimol, pyrifenox, triforine, flusilazole, etaconazole,dichlobutorazol, fluotrimazole, flutriafen, penconazole, diniconazole,imazalil, tridemorph, fenpropimorph, buthiobate, epoxiconazole,metoconazole, prothioconazole, spiroxamine, fenhexamid, pyributycarb,etc.

Antibiotic agents: polyoxins, blasticidin-S, kasugamycin, validamycin,dihydrostreptomycin sulfate, etc.

Anilide-based agents: boscalid, penthiopyrad, fluopyram, bixafen, etc.

Guanidine-based agents: iminoctadine acetate salt, iminoctadinealbesilate salt, dodine, guazatine, etc.

Valine-based agents: dimethomorph, flumorph, iprovalicarb,benthiavalicarb, mandipropamid, etc.

Others: cymoxanil, cyazofamid, amisulbrom, propamocarb, fluazinam,propamocarb acetate salt, ethaboxam, fluopicolide, zoxamide,cyflufenamid, metrafenone, proquinazid, hydroxy isoxazole,metasulfocarb, anilazine, isoprothiolane, ferimzone, probenazole,tiadinil, acibenzolar s-methyl, isotianil, pyroquilon, phthalide,tricyclazole, carpropamid, fenoxanil, diclocymet, fluazinam,fludioxonil, pyrrolenitrine, hydroxyl isoxazole, flusulfamide,diethofencarb, quintozene, metasulfocarb, anilazine, quinomethionate,dithianon, dinocap, dichlomezine, oxolinic acid, lecithin, sodiumbicarbonate, fenaminosulf, phenazine oxide, etc.

Insecticides/Acaricides:

Organic phosphorous and carbamate-based insecticides: fenthion,fenitrothion, diazinon, chlorpyrifos, ESP, vamidothion, phenthoate,dimethoate, formothion, malathion, trichlorfon, thiometon, phosmet,dichlorvos, acephate, EPBP, methyl parathion, oxydemeton-methyl, ethion,salithion, cyanophos, isoxathion, pyridafenthion, phosalone,methidathion, sulprofos, chlorfenvinphos, tetrachlorvinphos,dimethylvinphos, propaphos, isofenphos, ethylthiometon, profenofos,pyraclofos, monocrotophos, azinphos-methyl, aldicarb, methomyl,thiodicarb, carbofuran, carbosulfan, benfuracarb, furathiocarb,propoxur, BPMC, MTMC, MIPC, carbaryl, pirimicarb, ethiophencarb,fenoxycarb, etc.

Pyrethroid-based insecticides: permethrin, cypermethrin, deltamethrin,fenvalerate, fenpropathrin, pyrethrins, allethrin, tetramethrin,resmethrin, dimethrin, propathrin, phenothrin, prothrin, fluvalinate,cyfluthrin, cyhalothrin, flucythrinate, etofenprox, cycloprothrin,tralomethrin, silafluofen, Halfenprox, acrinathrin, etc.

Benzoylurea-based and other insecticides: diflubenzuron, chlorfluazuron,hexaflumuron, triflumuron, tetrabenzuron, flufenoxuron, flucycloxuron,buprofezin, pyriproxyfen, methoprene, benzoepin, diafenthiuron,acetamiprid, imidacloprid, nitenpyram, fipronil, cartap, thiocyclam,bensultap, nicotine sulfate, rotenone, metaldehyde, emamectin,flubendiamide, spinosad, machine oil, BT, insect pathogen viruses andother microbial agricultural chemicals, etc.

Nematicides: phenamiphos, fosthiazate, etc.

Acaricides: chlorobenzilate, phenisobromolate, dicofol, amitraz, BPPS,benzomate, hexathiazox, fenbutatin oxide, polynactin, quinomethionate,CPCBS, tetradifon, abamectin, milbemectin, clofentezine, cyhexatin,pyridaben, fenpyroximate, tebufenpyrad, pyrimidifen, fenothiocarb,dienochlor, fluacrypyrim, etc.

Plant Growth Regulators: gibberellins (e.g., gibberellin A3, gibberellinA4, gibberellin A7, etc.), IAA, NAA, etc.

EXAMPLES

The present invention will be explained in more detail by way ofExamples, but the present invention should not be interpreted to belimited to these Examples.

Preparation Example (Step 1)

A mixture of 2.94 g (11.4 mmol) of diethyl 4-chloro-2,6-pyridinedicarboxylate and 20 mL of ethanol was heated to 55° C. and an aqueoussolution prepared from 0.27 g (6.8 mmol) of sodium hydroxide and 50 mLof water was added dropwise to the mixture for 8 hours. After completionof the dropwise addition, the mixed solution was stirred for one hourand allowed to stand overnight at room temperature. After the solventwas removed under reduced pressure, the residue was back-extracted withwater/ethyl acetate. The organic layer was washed with water and theaqueous layers were combined. Then concentrated hydrochloric acid wasadded to the aqueous layer thereby adjusting the pH to 2.5. The aqueouslayer was extracted with ethyl acetate, washed with saturated brine andthen dried over anhydrous magnesium sulfate. The solvent was removedunder reduced pressure to obtain 1.42 g (6.2 mmol, yield of 54%) ofmonoethyl 4-chloro-2,6-pyridine dicarboxylate.

(Step 2)

To a mixture of 1.42 g (6.2 mmol) of monoethyl 4-chloro-2,6-pyridinedicarboxylate, 12 mL of anhydrous tetrahydrofuran and 0.69 g (6.8 mmol)of triethylamine, 1.87 g (6.8 mmol) of diphenyl phosphoryl azide wasadded at room temperature, followed by heating to 60° C. and furtherstirring for one hour.

To the reaction mixture, 0.93 g (12.6 mmol) of t-butanol was added,followed by further stirring at 60° C. for 18 hours. The reactionsolution was added to water, followed by extraction with ethyl acetate.The organic layer was washed with saturated brine and dried overanhydrous magnesium sulfate, and then the solvent was removed underreduced pressure. The residue was purified by silica gel columnchromatography (eluent: n-hexane/ethyl acetate=5/1 (v/v)) to obtain 1.00g (3.3 mmol, yield of 54%) of ethyl2-(t-butoxycarbonyl)amino-4-chloropicolinate.

(Step 3)

To a mixture of 1.00 g (3.3 mmol) of ethyl2-(t-butoxycarbonyl)amino-4-chloropicolinate and 20 mL of anhydrousethanol, 0.38 g (10.0 mmol) of sodium borohydride was added, followed bystirring at room temperature for 17 hours. To the reaction solution,dilute hydrochloric acid was added thereby adjusting the pH to 2 and thesolution was neutralized by adding saturated sodium bicarbonate aqueoussolution. After ethanol was removed under reduced pressure, theresultant was extracted with ethyl acetate and dried over anhydrousmagnesium sulfate. The solvent was removed under reduced pressure andthe resultant residue was purified by silica gel column chromatography(eluent: n-hexane/ethyl acetate=3/1 (v/v)) to obtain 0.75 g (2.9 mmol,yield of 87%) of2-(t-butoxycarbonyl)amino-4-chloro-6-hydroxymethylpyridine.

To a mixture of 0.74 g (2.9 mmol) of2-(t-butoxycarbonyl)amino-4-chloro-6-hydroxymethylpyridine and 20 mL ofdichloromethane 20 mL, 0.29 g (3.7 mmol) of pyridine was added, and 0.41g (3.5 mmol) of thionyl chloride was further added, followed by stirringat room temperature for 3.5 hours. The reaction solution was added towater and saturated sodium bicarbonate aqueous solution was addedthereby adjusting the pH to 6, followed by extraction with chloroform.The organic layer was dried over anhydrous magnesium sulfate and thesolvent was removed under reduced pressure. The resultant residue waspurified by silica gel column chromatography (eluent: n-hexane/ethylacetate=9/1 (v/v)) to obtain 0.56 g (2.0 mmol, yield of 71%) of2-(t-butoxycarbonyl)amino-4-chloro-6-chloromethylpyridine.

(Step 5)

A mixture of 5 mL of dry N,N-dimethylformamide and 0.12 g (0.6 mmol) of(Z)-(1-methyl-1H-tetrazol-5-yl)phenylmethanone oxime was cooled in anice bath and 0.03 g (60% in oil, 0.75 mmol) of sodium hydride was addedto the solution. After the suspension was stirred for 5 minutes, amixture of 0.19 g (0.69 mmol) of2-(t-butoxycarbonyl)amino-4-chloro-6-chloromethylpyridine and 5 mL ofN,N-dimethylformamide was added, followed by stirring at roomtemperature for 3 hours.

The reaction mixture was added to an aqueous saturated ammonium chloridesolution and then extracted with ethyl acetate. The organic layer wasdried over anhydrous magnesium sulfate and the solvent was removed underreduced pressure. The resultant residue was purified by silica gelcolumn chromatography (eluent: n-hexane/ethyl acetate=4/1 (v/v)) toobtain 0.16 g (0.3 mmol, yield of 62%) of(Z)-(1-methyl-1H-tetrazol-5-yl)phenylmethanone-0-[2-(t-butoxycarbonyl)amino-4-chloropyridin-6-ylmethyl]-oxime(compound of a compound number 1-275 in Table 1)

Although several Formulation Examples of the plant disease controllingagent of the present invention are shown below, additives and theadditive ratio should not be limited thereto and can be broadly changed.Parts shown in the Formulation Examples are by weight.

Formulation Example 1 Wettable Powders

Compound of the present invention 40 parts Clay 53 parts Sodium dioctylsulfosuccinate 4 parts Sodium lignin sulfonate 3 parts

The above components are uniformly mixed and finely ground to obtainwettable powders containing 40% of an active ingredient.

Formulation Example 2 Emulsifiable Concentrates

Compound of the present invention 10 parts Sorbesso 200 53 partsCyclohexanone 26 parts Calcium dodecylbenzene sulfonate 1 partPolyoxyethylene alkyl allyl ether 10 parts

The above components are mixed and dissolved to obtain emulsifiableconcentrates containing 10% of an active ingredient.

Formulation Example 3 Powders

Compound of the present invention 10 parts Clay 90 parts

The above components are uniformly mixed and finely ground to obtainpowders containing 10% of an active ingredient.

Formulation Example 4 Granules

Compound of the present invention 5 parts Clay 73 parts Bentonite 20parts Sodium dioctyl sulfosuccinate 1 part Potassium phosphate 1 part

The above components are well ground and mixed, well kneaded with water,granulated and then dried to obtain granules containing 5% of an activeingredient.

Formulation Example 5 Suspensions

Compound of the present invention 10 parts Polyoxyethylene alkyl allylether 4 parts Sodium polycarboxylate 2 parts Glycerin 10 parts Xanthangum 0.2 part Water 73.8 parts

The above components are mixed, and ground by wet grinding to a particlesize of 3 micron or less to obtain suspensions containing 10% of anactive ingredient.

Formulation Example 6 Granular Wettable Powders

Compound of the present invention 40 parts Clay 36 parts Potassiumchloride 10 parts Sodium alkylbenzene sulfonate 1 part Sodium ligninsulfonate 8 parts Formaldehyde condensate of sodium 5 parts alkylbenzenesulfonate

The above components are uniformly mixed and finely ground and thenkneaded with an appropriate amount of water to form a clay-likesubstance. The clay-like substance is granulated and then dried toobtain granular wettable powders containing 40% of an active ingredient.

Test Example Tomato Late Blight Control Test

An emulsifiable concentrate of Formulation Example 2 was sprayed overthe tomato seedling (cultivar: “Regina”, 4-5 leaves stage) grown in anunglazed pot, at the concentration of an active ingredient of 100 ppm.After spraying, the tomato seedling was air-dried at room temperatureand a zoosporangium suspension of tomato phytophthora (Phytophthorainfestans) was spray-inoculated, and then the tomato seedling wasretained in a high-humidity thermostatic chamber (20° C.) maintained ata light or dark state every 12 hours for 4 days. The state of appearanceof lesions on leaves was examined and compared with the non-treatedtomato seedling and thus the control effect was determined. As a result,the compounds shown below exhibited a preventive value of 80%. Thecompound numbers correspond to the compound numbers in Table 1.

Compound numbers: 1-17, 1-68 to 1-82, 1-84 to 1-87, 1-131, 1-197, 1-275to 1-278, 1-323, 1-377, 1-380, 1-399, 1-400, 1-405 to 1-407, 1-415,1-418, 1-420 to 1-424, 1-429 to 1-431, 1-435, 1-445 to 1-450, 1-452 to1-460, 1-464, 1-467 to 1-479, 1-481, 1-486, 1-488, and 1-491

INDUSTRIAL APPLICABILITY

The present invention provides a tetrazoyloxime derivative or a saltthereof, which is excellent in a control effect against plant diseaseinjury, and a plant disease controlling agent containing the same as anactive ingredient, and is therefore industrially quite useful.

The invention claimed is:
 1. A tetrazoyloxime derivative represented byformula (1):

wherein A represents a tetrazoyl group represented by formula (2):

in which Y represents a C₁₋₈ alkyl group; and Het represents a pyridylgroup represented by formula (4):

in which Z represents a group represented by formula: Q¹C(═O)NH— (inwhich Q¹ represents a C₅₋₆ alkenyloxy group, or a C₄₋₇ alkynyloxygroup), or a salt thereof.
 2. The tetrazoyloxime derivative according toclaim 1, wherein Y is a methyl group, or a salt thereof.